CN103553978A - Sulfamide benzylation method - Google Patents
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- CN103553978A CN103553978A CN201310500639.1A CN201310500639A CN103553978A CN 103553978 A CN103553978 A CN 103553978A CN 201310500639 A CN201310500639 A CN 201310500639A CN 103553978 A CN103553978 A CN 103553978A
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Abstract
The invention relates to a sulfamide benzylation method. According to the sulfamide benzylation method, a finished product is obtained through reaction, concentration and purification by taking various benzyl alcohols and sulfamide as raw materials, boron trifluoride diethyl etherate as a reaction reagent and trichloromethane as a solvent. The sulfamide benzylation method disclosed by the invention has the characteristics of simple method, easiness and convenience for operation, no metal participating reaction, high yield, convenience for application and popularization, and the like, greatly reduces the synthesis cost by taking low-cost benzyl alcohol as a benzylation reagent, can be used for preparing benzyl sulfonamide products with high output rate and multiple varieties and can be widely applied to the industrialized production of benzyl sulfonamides; the product prepared through the sulfamide benzylation method disclosed by the invention can be widely applied to the fields of medicines, pesticides, dyes, engineering plasticizing agents, sterilizing agents, chemical raw materials, and the like and meets the requirements for wide range and large number of the market.
Description
Technical field
The invention belongs to organic chemical synthesis technical field, be specifically related to the method for sulphonamide benzyl.
Background technology
Sulphonamide is important medicine, pesticide efficacy group, and its derivative is usually to have bioactive compound.In recent years, sulfone amide derivative is widely applied in productive life, as: weeding, sterilization, desinsection, anticancer, anti-diabetic etc.In addition, sulfone amide derivative is also used as softening agent and the dyestuff of engineering materials.
The method of existing sulfonamides benzyl, as publication number in 2012 " a kind of method of alcohol and the amine dehydration synthesizing aminated compounds " patent that is CN102617259A, the disclosed method of this patent is that to utilize sulphonamide and alcohol be raw material, take the aldehyde corresponding with reactant alcohol and an alkali metal salt is catalyzer, by gas chromatography mass spectrometry and thin-layer chromatography chromatogram tracking, detect, through column chromatography for separation, obtain product.But mainly there is following deficiency in the method:
(1) this temperature of reaction is up to 200 ℃, and energy consumption is large, and production cost is high.
(2) the method is reacted the length that expends time in, and is unfavorable for suitability for industrialized production.
(3) the method relates to metal participation.
Summary of the invention
The object of the invention is the weak point for existing N-benzyl sulfonamide compounds synthetic method, a kind of method of sulphonamide benzyl is provided.It is raw material that the method be take benzylalcohol, sulphonamide, and boron trifluoride diethyl etherate is reaction reagent, and synthetic method has certain universality, and multiple sulphonamide and the reaction of multiple benzylalcohol can obtain good productive rate.Present method reaction conditions is gentle, and low to production unit requirement, technique is simple, preparation feedback production safety, and easily operation, raw material is easy to get, and the reaction times is short, and efficiency is higher, purifies simple, is conducive to industrialization.
The technical scheme that realizes the object of the invention is: a kind of method of sulphonamide benzyl, and take benzylalcohol, sulphonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, through electrophilic substitution reaction, generates sulphonamide benzyl derivative.Its concrete method steps is as follows:
(1) carry out substitution reaction
Take benzylalcohol, sulphonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, according to benzylalcohol mmole: sulphonamide mmole: BF
3oEt
2mmole: the ratio of solvent milliliter is (1.0～1.5): (1.0～1.8): (0.2～1.5): 2 ratio, in reactor, successively add benzylalcohol, sulphonamide and solvent, under stirring, add again BF
3oEt
2, reinforced complete, at 60～120 ℃, continue stirring reaction 2～4.5 hours, prepare the reaction solution of benzyl sulphonamide.
Described solvent is a kind of in trichloromethane, hexanaphthene, toluene, DMF, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), ether, ethyl acetate, Isosorbide-5-Nitrae-dioxane, methylene dichloride, ethylene dichloride.
(2) say that row product is concentrated, purifying
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, is rotated evaporation concentration, collects concentrated solution; Concentrated solution, through purification by silica gel column chromatography, carries out wash-out with elutriant, and the effluent liquid of silica gel column chromatography is concentrated, drains and to obtain product (I) through rotary evaporation.
R in formula (I)
1for alkyl, aryl, R
2for benzyl.
The present invention adopts after technique scheme, mainly contains following effect:
(1) benzylalcohol raw material sources are extensive, are cheaply easy to get, and structure is abundant, are easy to obtain the sulfone amide derivative of various benzyls, can meet the multifarious demand of benzyl sulphonamide kind.
(2) by product is few, and product is easy to purifying, avoids metal ion and participates in.
(3) reaction conditions is gentle, and without protection of inert gas, preparation technology and lock out operation are simple, with low cost, and substrate universality is strong, easy to utilize.
(4) product obtain only needing single stepping, yield is higher, good product quality is convenient to suitability for industrialized production, can meet the demand having a large capacity and a wide range in market.
The inventive method can be widely used in the suitability for industrialized production of benzyl sulphonamide.The product that adopts the inventive method to prepare can be widely used in the fields such as medicine, agricultural chemicals, dyestuff, engineering softening agent, sterilant and industrial chemicals, meets the various lots of needs in market.
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1
A method for sulphonamide benzyl, its concrete steps are as follows:
(1) take phenylcarbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8:1.2: 2 ratio successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
After (2) (1) steps complete, the reaction solution of the benzyl sulphonamide that (1) step is prepared, is rotated evaporation concentration, collects concentrated solution; Concentrated solution, through purification by silica gel column chromatography, carries out wash-out with elutriant, and the effluent liquid of silica gel column chromatography is concentrated, drains and to obtain white solid N-benzyl para toluene sulfonamide (215mg, yield 82%) through rotary evaporation.
Described elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40).
Embodiment 2
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, benzsulfamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: benzsulfamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is the ratio of 1:1.8: 1.2:2 successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, benzsulfamide (282.9mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-benzyl benzsulfamide (171mg, yield 69%).
Embodiment 3
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, Toluidrin is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: Toluidrin mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1: 1.8: the ratio of 1.2:2 successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, Toluidrin (171.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-benzyl Toluidrin (144mg, yield 78%).
Embodiment 4
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, orthotoluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: orthotoluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1: the ratio of 1.8:1.2:2 successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, orthotoluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40), obtains white solid N-benzyl orthotoluene sulfonamide (190mg, yield 73%).
Embodiment 5
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take to chlorobenzene methanol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to chlorobenzene methanol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8: the ratio of 1.2: 2 successively adds chlorobenzene methanol (142.6mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-(4-chlorophenylmethyl) para toluene sulfonamide (239mg, yield 81%).
Embodiment 6
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take to fluorophenyl methanol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to fluorophenyl methanol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is the ratio of 1:1.8: 1.2:2 successively adds fluorophenyl methanol (126.1mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40), obtains white solid N-(4-fluorobenzene methyl) para toluene sulfonamide (226mg, yield 81%).
Embodiment 7
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take adjacent iodobenzene methyl alcohol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to adjacent iodobenzene methyl alcohol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio that the ratio of trichloromethane milliliter is 1:1.8:1.2:2 successively adds adjacent iodobenzene methyl alcohol (234mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 4.5 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-(4-iodobenzene methyl) para toluene sulfonamide (171mg, yield 44%).
Embodiment 8
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take to bromobenzene methyl alcohol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to bromobenzene methyl alcohol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is the ratio of 1:1.8: 1.2:2 successively adds bromobenzene methyl alcohol (t87mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-(4-Brombenzyl) para toluene sulfonamide (228mg, yield 67%).
Embodiment 9
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take to methylbenzene methanol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to methylbenzene methanol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8:1.2: 2 ratio successively adds methylbenzene methanol (122.2mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-(4-methylbenzene methyl) para toluene sulfonamide (140mg, yield 51%).
Embodiment 10
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take adjacent chlorobenzene methanol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to adjacent chlorobenzene methanol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8:1.2: 2 ratio successively adds adjacent chlorobenzene methanol (142.6mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40), obtains white solid N-(2-chlorophenylmethyl) para toluene sulfonamide (154.3mg, yield 52%).
Embodiment 11
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take 2,4-DCBA, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to 2,4-DCBA mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8: the ratio of 1.2: 2 successively adds 2,4-DCBA (177.0mg in reactor, 1.0mmol), para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 3 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-(2,4 dichloro benzene methyl) para toluene sulfonamide (110mg, yield 33%).
Embodiment 12
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take a chloro-methyl phenyl carbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to a chloro-methyl phenyl carbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio that the ratio of trichloromethane milliliter is 1:1.8:1.2:2, chloro-methyl phenyl carbinol (156.6mg, 1.0mmol) between successively adding in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40), obtains white solid N-(the chloro-α-styroyl of 3-) para toluene sulfonamide (248mg, yield 80%).
Embodiment 13
A method for sulphonamide benzyl, its concrete steps are as follows:
In step (1), take phenylcarbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1.5: 1.0: the ratio of 1.2:2 successively adds phenylcarbinol (162.2mg, 1.0mmol) in reactor, para toluene sulfonamide (171.2mg, 1.0mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, take sym-trimethylbenzene as interior mark, by nucleus magnetic hydrogen spectrum, determines that product N-benzyl para toluene sulfonamide yield is 49%.
Embodiment 14
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1: 1.8: the ratio of 1.2:2 successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 60 ℃, continue stirring reaction 2 hours.
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, take sym-trimethylbenzene as interior mark, by nucleus magnetic hydrogen spectrum, determines that product N-benzyl para toluene sulfonamide yield is 72%.
Embodiment 15
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio that the ratio of trichloromethane milliliter is 1:1.8:1.2:2 successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, para toluene sulfonamide (308.2mg, 1.8mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(151 μ L, 1.2mmol), reinforced complete, at 120 ℃, continue stirring reaction 2 hours.
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, take sym-trimethylbenzene as interior mark, by nucleus magnetic hydrogen spectrum, determines that product N-benzyl para toluene sulfonamide yield is 52%.
Embodiment 16
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and ethylene dichloride is made solvent, according to phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of ethylene dichloride milliliter is 1: 1.0: 0.2: 2 ratio successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, para toluene sulfonamide (171.2mg, 1.0mmol) and ethylene dichloride (2.0mL), under stirring, then add BF
3oEt
2(25 μ L, 0.2mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, take sym-trimethylbenzene as interior mark, by nucleus magnetic hydrogen spectrum, determines that product N-benzyl para toluene sulfonamide yield is 12%.
Embodiment 17
A method for sulphonamide benzyl, its concrete steps are with embodiment 1, wherein:
In step (1), take phenylcarbinol, para toluene sulfonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, and trichloromethane is made solvent, according to phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio that the ratio of trichloromethane milliliter is 1:1.5:1.5:2 successively adds phenylcarbinol (108.1mg, 1.0mmol) in reactor, para toluene sulfonamide (256.8mg, 1.5mmol) and trichloromethane (2.0mL), under stirring, then add BF
3oEt
2(188 μ L, 1.5mmol), reinforced complete, at 80 ℃, continue stirring reaction 2 hours.
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, take sym-trimethylbenzene as interior mark, by nucleus magnetic hydrogen spectrum, determines that product N-benzyl para toluene sulfonamide yield is 62%.
Embodiment 18-28
Concrete steps for the method for benzyl, with embodiment 1, different piece is wherein as shown in the table.
Table 1
Claims (5)
1. a method for sulphonamide benzyl, is characterized in that concrete method steps is as follows:
(1) carry out substitution reaction
Take benzylalcohol, sulphonamide is raw material, and boron trifluoride diethyl etherate is reaction reagent, according to benzylalcohol mmole: sulphonamide mmole: BF
3oEt
2mmole: the ratio of solvent milliliter is (1.0～1.5): (1.0～1.8): (0.2～1.5): 2 ratio, in reactor, successively add benzylalcohol, sulphonamide and solvent, under stirring, add again BF
3oEt
2, reinforced complete, at 60～120 ℃, continue stirring reaction 2～4.5 hours, prepare the reaction solution of benzyl sulphonamide;
Described solvent is a kind of in trichloromethane, hexanaphthene, toluene, DMF, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), ether, ethyl acetate, Isosorbide-5-Nitrae-dioxane, methylene dichloride, ethylene dichloride;
(2) carry out that product is concentrated, purifying
After (1) step completes, the reaction solution of the benzyl sulphonamide that (1) step is prepared, is rotated evaporation concentration, collects concentrated solution; Concentrated solution, through purification by silica gel column chromatography, carries out wash-out with elutriant, and the effluent liquid of silica gel column chromatography is concentrated, drains and to obtain product through rotary evaporation;
Described elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40).
2. according to the method for a kind of sulphonamide benzyl claimed in claim 1, it is characterized in that: in step (1), raw material is phenylcarbinol, para toluene sulfonamide, and reaction reagent is boron trifluoride diethyl etherate, solvent is trichloromethane, phenylcarbinol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1: 1.8:1.2:2 continues stirring reaction 2 hours at 80 ℃;
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-benzyl para toluene sulfonamide.
3. according to the method for a kind of sulphonamide benzyl claimed in claim 1, it is characterized in that: in step (1), raw material is to chlorobenzene methanol, para toluene sulfonamide, reaction reagent is boron trifluoride diethyl etherate, solvent is trichloromethane, to chlorobenzene methanol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8:1.2:2 continues stirring reaction 2 hours at 80 ℃;
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40) mixed solution, obtain white solid N-(4-chlorophenylmethyl) para toluene sulfonamide.
4. according to the method for a kind of sulphonamide benzyl claimed in claim 1, it is characterized in that: in step (1), raw material is to fluorophenyl methanol, para toluene sulfonamide, reaction reagent is boron trifluoride diethyl etherate, solvent is trichloromethane, to fluorophenyl methanol mmole: para toluene sulfonamide mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1:1.8: 1.2:2 continues stirring reaction 2 hours at 80 ℃;
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1: the mixed solution of (2～40), obtains brilliant white solid N-(4-fluorobenzene methyl) para toluene sulfonamide.
5. according to the method for a kind of sulphonamide benzyl claimed in claim 1, it is characterized in that: in step (1), raw material is phenylcarbinol, brosyl amine, and reaction reagent is boron trifluoride diethyl etherate, solvent is trichloromethane, phenylcarbinol mmole: brosyl amine mmole: BF
3oEt
2mmole: the ratio of trichloromethane milliliter is 1: 1.8: 1.2:2 continues stirring reaction 2 hours at 80 ℃;
In step (2), elutriant is ethyl acetate: sherwood oil volume ratio is 1:(2～40), obtain white solid N-benzyl brosyl amine.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409612A (en) * | 2018-03-21 | 2018-08-17 | 福建医科大学 | A kind of method that N- benzyl benzenesulfonamides are catalyzed and synthesized by boric acid/Catalyzed by Oxalic Acid system under microwave radiation |
| CN112110837A (en) * | 2020-08-19 | 2020-12-22 | 曲靖师范学院 | Method for synthesizing organic sulfone molecule by using novel sulfone benzylation reagent |
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| VINCENT TERRASSON，ET AL: "Lewis Acid-Catalyzed Direct Amination of Benzhydryl Alcohols", 《ADV. SYNTH. CATAL.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409612A (en) * | 2018-03-21 | 2018-08-17 | 福建医科大学 | A kind of method that N- benzyl benzenesulfonamides are catalyzed and synthesized by boric acid/Catalyzed by Oxalic Acid system under microwave radiation |
| CN112110837A (en) * | 2020-08-19 | 2020-12-22 | 曲靖师范学院 | Method for synthesizing organic sulfone molecule by using novel sulfone benzylation reagent |
| CN112110837B (en) * | 2020-08-19 | 2022-04-22 | 曲靖师范学院 | Method for synthesizing organic sulfone molecule by using novel sulfone benzylation reagent |
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