CN108299259B - Preparation method of 2-amino-5-thiophenyl- (2-methoxy) acetanilide - Google Patents
Preparation method of 2-amino-5-thiophenyl- (2-methoxy) acetanilide Download PDFInfo
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Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-amino-5-thiophenyl- (2-methoxy) acetanilide. The invention uses 2-nitro-5-mercaptoaniline and halogenated benzene to prepare 2-nitro-5-thiophenyl aniline, then reacts with 2-methoxy methyl acetate to obtain 2-nitro-5-thiophenyl- (2-methoxy) acetanilide, and finally obtains the target product through catalytic hydrogenation reduction. The method has good reaction selectivity, and the obtained target product has high purity and yield; the use of high-toxicity materials is avoided, the requirements on equipment and operating conditions are reduced, and the safety and the stability of the preparation method are improved; the using amount of the reaction materials is optimized, and the excessive halogenated benzene and the 2-methoxy methyl acetate can be recycled after simple recovery; the produced solid waste is less, the waste treatment cost is greatly reduced, and the requirements of environmental protection are met.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-amino-5-thiophenyl- (2-methoxy) acetanilide.
Background
Febantel is a veterinary anthelmintic agent and can be used for repelling nematodes, adults and larvae in animals such as dogs, sheep, pigs, horses and the like. Febantel does not itself have anthelmintic activity but exerts its anthelmintic effect by conversion in animals to fenbendazole, fenbendazole sulfoxide and oxfendazole sulfone. Febantel, which has the same action and application as fenbendazole, structurally has a strong affinity for the tubulin of the polypide and is significantly higher than that of mammal tubulin, so that microtubules can be prevented from polymerizing, the transport system of absorbed cells can be damaged, and finally, the absorption and digestion of nutrient particles are incomplete through the activation of various lysosomal enzymes (Iysosomal enzymes), so that the cells can be decomposed automatically, and the insect repellent effect can be realized.
2-amino-5-thiophenyl- (2-methoxy) acetanilide is an important intermediate for synthesizing febantel. In the prior art, the febantel intermediate 2-amino-5-phenylthio- (2-methoxy) acetanilide is generally synthesized by the following process steps:
condensing 5-chloro-2-nitroaniline and thiophenol under an alkaline condition to obtain 2-nitro-5-thiophenyl aniline, then reacting with acylating agent 2-methoxyacetyl chloride to obtain 2-nitro-5-thiophenyl- (2-methoxy) acetanilide, and finally reducing nitro on a benzene ring by hydrazine hydrate to obtain 2-amino-5-thiophenyl- (2-methoxy) acetanilide.
The method has high yield and product purity, but high-toxicity chemicals such as thiophenol, 5-chloro-2-nitroaniline, 2-methoxyacetyl chloride, hydrazine hydrate and the like are required to be used in the preparation process, and the requirements on production equipment and operation are high. In addition, in order to achieve higher yields in each reaction step, large excesses of reaction materials (thiophenol, 2-methoxyacetyl chloride, hydrazine hydrate) are generally required, with low economic availability and great environmental hazard.
In addition, the nitro group on the benzene ring can be reduced by methods such as iron powder reduction, electrochemical reduction, alkali sulfide reduction, and noble metal catalytic reduction (palladium, platinum, ruthenium, etc.). However, these methods are either eliminated due to environmental pollution and inconvenient production operations, or have not been applied on a large scale due to high energy consumption and severe equipment requirements, or have limited application range due to the lack of economic value due to expensive and easily poisoned catalysts.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of 2-amino-5-thiophenyl- (2-methoxy) acetanilide, which is environment-friendly, easy to industrialize and has higher economic value.
The invention is realized by the following technical scheme:
the preparation method of the 2-amino-5-thiophenyl- (2-methoxy) acetanilide comprises the following steps:
(1) preparation of 2-nitro-5-thiophenylaniline: mixing 2-nitro-5-mercaptoaniline, potassium carbonate and halogenated benzene in a reaction vessel, introducing inert gas for protection, and stirring and refluxing at 130-160 ℃ until the reaction is complete; filtering to remove insoluble substances, cooling the filtrate to-20-5 ℃, stirring, and separating out 2-nitro-5-thiophenyl aniline crystals;
(2) preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: mixing 2-nitro-5-thiophenylaniline and 2-methoxy methyl acetate, filling inert gas for protection, and stirring and reacting at 100-130 ℃ until the reaction is complete; cooling to below 70 deg.C, adding alkane solvent, stirring, and separating out crystal 2-nitro-5-thiophenyl- (2-methoxy) acetanilide;
(3) preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: mixing 2-nitro-5-thiophenyl- (2-methoxy) acetanilide, an iron/nickel supported catalyst and an organic solvent in a reaction vessel, introducing hydrogen to ensure that the pressure of the hydrogen in the reaction vessel is 0.1-2.0MPa, and stirring and reacting at 15-45 ℃ until the reaction is complete; filtering to remove the catalyst, adding purified water into the filtrate, cooling to 0-5 ℃, stirring, and precipitating 2-amino-5-thiophenyl- (2-methoxy) acetanilide crystals.
Preferably, the mass ratio of the halogenated benzene to the 2-nitro-5-mercaptoaniline is 3.0-10.0, and the use amount of the potassium carbonate is 0.5-3.0 times of the molar amount of the 2-nitro-5-mercaptoaniline.
Further preferably, the mass ratio of the halogenated benzene to the 2-nitro-5-mercaptoaniline is 4.0-5.0, and the use amount of the potassium carbonate is 1.0 time of the molar amount of the 2-nitro-5-mercaptoaniline.
Preferably, the halogenated benzene is one of chlorobenzene or bromobenzene.
Further preferably, the halogenated benzene is chlorobenzene.
Preferably, the filtrate in the step (1) is cooled to 0-5 ℃.
Preferably, the mass ratio of the 2-methoxy methyl acetate to the 2-nitro-5-thiophenyl aniline is 2.0-10.0, and the mass ratio of the alkane solvent to the 2-methoxy methyl acetate is 1.0-5.0.
More preferably, the mass ratio of the methyl 2-methoxyacetate to the 2-nitro-5-thiophenylaniline is 3.0-5.0, and the mass ratio of the alkane solvent to the methyl 2-methoxyacetate is 1.0-2.0.
Preferably, the alkane solvent is one or a mixture of C5-C8 alkane.
Further preferably, the alkane solvent is one or more of n-pentane, n-hexane, n-heptane and isooctane.
More preferably, the alkane solvent is one or a mixture of n-hexane and n-heptane.
Preferably, the reaction temperature of the step (2) is 110-120 ℃.
Preferably, the mass ratio of the organic solvent to the 2-nitro-5-thiophenyl- (2-methoxy) acetanilide is 3.0-15.0.
Further preferably, the mass ratio of the organic solvent to the 2-nitro-5-thiophenyl- (2-methoxy) acetanilide is 5.0 to 6.0.
Preferably, the organic solvent is one or more of methanol, ethanol and propanol.
Preferably, the reaction temperature of the step (3) is 20-30 ℃.
The invention has the beneficial effects that:
(1) the preparation method has good reaction selectivity, the purity of the obtained target product is more than or equal to 99.0 percent, and the total yield of the three-step reaction is 30.8 to 85.8 percent;
(2) compared with 5-chloro-2-nitroaniline and thiophenol, the starting materials of the preparation method are 2-nitro-5-mercaptoaniline and halogenated benzene, so that the use of highly toxic chemical thiophenol is avoided; 2-methoxy methyl acetate is used as the acylating agent to replace 2-methoxy acetyl chloride, so that the requirements of the reaction process on equipment and operation conditions are reduced; the catalytic hydrogenation method is used for replacing hydrazine hydrate to reduce the nitro group on the benzene ring, so that the use of high-toxicity material hydrazine hydrate is avoided, and the safety and stability of the preparation process are improved;
(3) the preparation method optimizes the use amount of the reaction materials, and the excessive halogenated benzene and 2-methoxy methyl acetate can be recycled after simple recovery;
(4) the preparation method of the invention generates less solid waste, greatly reduces the waste treatment cost, and the whole preparation method is more in line with the requirements of environmental protection.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
(1) Preparation of 2-nitro-5-thiophenylaniline: adding 2-nitro-5-mercaptoaniline (17.0g), potassium carbonate (13.8g) and chlorobenzene (85.0g) into a 250ml reaction bottle provided with a thermometer, a water separator, a condenser and a stirring device, introducing nitrogen for three times for replacement, heating to 130-135 ℃, stirring and carrying out reflux reaction for 3-5 hours; filtering while the solution is hot, stirring the filtrate, cooling the filtrate to 0-5 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl aniline with the yield of 95.4%;
(2) preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenylaniline (24.7g) and methyl 2-methoxyacetate (123.0g) into a 500ml reaction bottle provided with a thermometer, a condenser and a stirring device, introducing nitrogen for three times for replacement, stirring and heating to 120-130 ℃ for reaction for 5-7 hours; cooling to below 70 ℃, dropwise adding n-hexane (200ml), cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain 2-nitro-5-thiophenyl- (2-methoxy) acetanilide with the yield of 95.5%;
(3) preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenyl- (2-methoxy) acetanilide (32.0g), an iron/nickel supported catalyst (with the content of 10 percent and the content of 3.2g) and methanol (200ml) into a 500ml stainless steel high-pressure reaction kettle, starting stirring, firstly introducing nitrogen for three times, then introducing hydrogen for three times, and finally introducing hydrogen until the pressure in the reaction kettle is 0.5 MPa; maintaining the temperature of the reaction kettle at 25-35 ℃ and the internal pressure at 0.1-0.5 MPa, and stirring for reaction for 12 hours until the reaction is complete; and filtering the reaction solution, collecting filtrate, dropwise adding purified water (100ml) while stirring, then cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-amino-5-thiophenyl- (2-methoxy) acetanilide with the purity of more than 99.0% and the yield of 94.2%.
Example 2
(1) Preparation of 2-nitro-5-thiophenylaniline: adding 2-nitro-5-mercaptoaniline (85.0g), potassium carbonate (69.1g) and bromobenzene (340.0g) into a 1000ml reaction bottle provided with a thermometer, a water separator, a condenser and a stirring device, introducing nitrogen for replacement for three times, and stirring and refluxing at 150-160 ℃ for 5-6 hours; and filtering while the solution is hot, stirring the filtrate, cooling to-5-0 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl aniline with the yield of 94.3%.
(2) Preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenylaniline (123.1g) and methyl 2-methoxyacetate (500.0g) into a 2000ml reaction bottle provided with a thermometer, a condenser and a stirring device, introducing nitrogen for three times for replacement, stirring and heating to 110-120 ℃ for reaction for 8-10 hours; cooling to below 70 ℃, dropwise adding n-heptane (1000ml), cooling to 0-5 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl- (2-methoxy) acetanilide with the yield of 90.3%.
(3) The preparation method of the 2-amino-5-thiophenyl- (2-methoxy) acetanilide comprises the steps of adding 159.2g of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide, 16.0g of iron/nickel supported catalyst and 1200ml of ethanol into a 2L stainless steel high-pressure reaction kettle, starting stirring, introducing nitrogen for three times, then introducing hydrogen for three times, finally introducing hydrogen until the pressure in the reaction kettle is 0.5MPa, maintaining the temperature of the reaction kettle at 20-30 ℃ and the internal pressure at 0.1-0.5 MPa, stirring for 20 hours until the reaction is complete, filtering the reaction liquid, collecting filtrate, dropwise adding 240ml of purified water while stirring, then cooling to 0-5 ℃, continuing to stir for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-amino-5-thiophenyl- (2-methoxy) acetanilide with the purity of 99.0% and the yield of 85.0%.
Example 3
(1) Preparation of 2-nitro-5-thiophenylaniline: adding 2-nitro-5-mercaptoaniline (17.0g), potassium carbonate (27.5g) and chlorobenzene (170.0g) into a 500ml reaction bottle provided with a thermometer, a water separator, a condenser and a stirring device, introducing nitrogen for three times for replacement, heating to 130-135 ℃, stirring and carrying out reflux reaction for 3-5 hours; filtering while hot, stirring the filtrate to reduce the temperature to-20-10 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl aniline with the yield of 89.5 percent;
(2) preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenylaniline (24.7g) and methyl 2-methoxyacetate (50.0g) into a 250ml reaction bottle provided with a thermometer, a condenser and a stirring device, introducing nitrogen for three times for replacement, stirring and heating to 120-130 ℃ for reaction for 5-7 hours; cooling to below 70 ℃, dropwise adding n-hexane (50ml), cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain 2-nitro-5-thiophenyl- (2-methoxy) acetanilide with the yield of 85.8%;
(3) preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenyl- (2-methoxy) acetanilide (32.0g), an iron/nickel supported catalyst (with the content of 10 percent and the content of 3.2g) and n-propanol (480ml) into a 1000ml stainless steel high-pressure reaction kettle, starting stirring, firstly introducing nitrogen for replacing three times, then introducing hydrogen for replacing three times, and finally introducing hydrogen until the pressure in the reaction kettle is 0.5 MPa; maintaining the temperature of the reaction kettle at 30-45 ℃ and the internal pressure at 0.1-0.5 MPa, and stirring for reaction for 24 hours until the reaction is complete; and filtering the reaction solution, collecting filtrate, dropwise adding purified water (100ml) while stirring, then cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-amino-5-thiophenyl- (2-methoxy) acetanilide with the purity of more than 99.0% and the yield of 74.5%.
Example 4
(1) Preparation of 2-nitro-5-thiophenylaniline: adding 2-nitro-5-mercaptoaniline (17.0g), potassium carbonate (7.5g) and chlorobenzene (51.0g) into a 250ml reaction bottle provided with a thermometer, a water separator, a condenser and a stirring device, introducing nitrogen for three times for replacement, heating to 130-135 ℃, stirring and carrying out reflux reaction for 3-5 hours; filtering while hot, stirring the filtrate to reduce the temperature to-15-5 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl aniline with the yield of 80.2 percent;
(2) preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenylaniline (24.7g) and methyl 2-methoxyacetate (240.0g) into a 500ml reaction bottle provided with a thermometer, a condenser and a stirring device, introducing nitrogen for three times for replacement, starting stirring, heating to 120-130 ℃ and reacting for 6-8 hours; cooling to below 70 ℃, dropwise adding n-hexane (60ml), cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain 2-nitro-5-thiophenyl- (2-methoxy) acetanilide with the yield of 45.0%;
(3) preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenyl- (2-methoxy) acetanilide (22.0g), iron/nickel supported catalyst (content: 10%, 2.5g) and methanol (200ml) into a 500ml stainless steel high-pressure reaction kettle, starting stirring, introducing nitrogen for three times, then introducing hydrogen for three times, and finally introducing hydrogen until the pressure in the reaction kettle is 0.5 MPa; maintaining the temperature of the reaction kettle at 15-30 ℃ and the internal pressure at 0.1-0.5 MPa, and stirring for reaction for 14 hours until the reaction is complete; and filtering the reaction solution, collecting filtrate, dropwise adding purified water (200ml) while stirring, then cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-amino-5-thiophenyl- (2-methoxy) acetanilide with the purity of 90.0% and the yield of 85.5%.
Example 5
(1) Preparation of 2-nitro-5-thiophenylaniline: adding 2-nitro-5-mercaptoaniline (17.0g), potassium carbonate (10.5g) and bromobenzene (170.0g) into a 250ml reaction bottle provided with a thermometer, a water separator, a condenser and a stirring device, introducing nitrogen for replacement for three times, heating to 130-140 ℃, and stirring for reaction for 3-5 hours; filtering while the solution is hot, stirring the filtrate, cooling to-10-0 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl aniline with the yield of 72.0%;
(2) preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenylaniline (26.0g) and methyl 2-methoxyacetate (130.0g) into a 250ml reaction bottle provided with a thermometer, a condenser and a stirring device, introducing nitrogen for three times for replacement, stirring and heating to 120-130 ℃ for reaction for 7-9 hours; cooling to below 70 ℃, dropwise adding n-hexane (85ml), cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain 2-nitro-5-thiophenyl- (2-methoxy) acetanilide with the yield of 88.0%;
(3) preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenyl- (2-methoxy) acetanilide (35.0g), iron/nickel supported catalyst (content: 10%, 2.5g) and ethanol (210ml) into a 500ml stainless steel high-pressure reaction kettle, starting stirring, introducing nitrogen for three times, then introducing hydrogen for three times, and finally introducing hydrogen until the pressure in the reaction kettle is 0.5 MPa; maintaining the temperature of the reaction kettle at 25-35 ℃ and the internal pressure at 0.1-0.5 MPa, and stirring for reacting for 18 hours until the reaction is complete; and filtering the reaction solution, collecting filtrate, dropwise adding purified water (100ml) while stirring, then cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-amino-5-thiophenyl- (2-methoxy) acetanilide with the purity of 92.0% and the yield of 91.5%.
Example 6
(1) Preparation of 2-nitro-5-thiophenylaniline: adding 2-nitro-5-mercaptoaniline (35.0g), potassium carbonate (28.0g) and chlorobenzene (140.0g) into a 250ml reaction bottle provided with a thermometer, a water separator, a condenser and a stirring device, introducing nitrogen for three times for replacement, and stirring and refluxing at 150-160 ℃ for 5-6 hours for reaction; and filtering while the solution is hot, stirring the filtrate, cooling to-5-0 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl aniline with the yield of 93.5%.
(2) Preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenylaniline (23.5g) and methyl 2-methoxyacetate (75.0g) into a 100ml reaction bottle provided with a thermometer, a condenser and a stirring device, introducing nitrogen for three times for replacement, starting stirring, heating to 120-130 ℃, and reacting for 5-6 hours until the reaction is complete; cooling to below 70 ℃, dropwise adding n-heptane (25ml), cooling to 0-5 ℃, continuing stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-nitro-5-thiophenyl- (2-methoxy) acetanilide with the yield of 80.0%.
(3) Preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: adding 2-nitro-5-thiophenyl- (2-methoxy) acetanilide (16.0g), iron/nickel supported catalyst (content: 10%, 1.6g) and methanol (160ml) into a 500ml stainless steel high-pressure reaction kettle, starting stirring, introducing nitrogen for three times, then introducing hydrogen for three times, and finally introducing hydrogen until the pressure in the reaction kettle is 0.5 MPa; maintaining the temperature of the reaction kettle at 20-30 ℃ and the internal pressure at 0.1-0.5 MPa, and stirring for reaction for 15 hours until the reaction is complete; and filtering the reaction solution, collecting filtrate, dropwise adding purified water (60ml) while stirring, then cooling to 0-5 ℃, continuously stirring for 1 hour, filtering, collecting precipitated crystals, washing and drying to obtain the 2-amino-5-thiophenyl- (2-methoxy) acetanilide with the purity of more than 99.0% and the yield of 90.0%.
Claims (8)
- A process for producing 2-amino-5-phenylthio- (2-methoxy) acetanilide, which comprises the steps of:(1) preparation of 2-nitro-5-thiophenylaniline: mixing 2-nitro-5-mercaptoaniline, potassium carbonate and halogenated benzene in a reaction vessel, introducing inert gas for protection, and stirring and refluxing at 130-160 ℃ until the reaction is complete; filtering to remove insoluble substances, cooling the filtrate to-20-5 ℃, stirring, and separating out 2-nitro-5-thiophenyl aniline crystals;(2) preparation of 2-nitro-5-thiophenyl- (2-methoxy) acetanilide: mixing 2-nitro-5-thiophenylaniline and 2-methoxy methyl acetate, filling inert gas for protection, and stirring and reacting at 100-130 ℃ until the reaction is complete; cooling to below 70 deg.C, adding alkane solvent, stirring, and separating out crystal 2-nitro-5-thiophenyl- (2-methoxy) acetanilide;(3) preparation of 2-amino-5-thiophenyl- (2-methoxy) acetanilide: mixing 2-nitro-5-thiophenyl- (2-methoxy) acetanilide, an iron/nickel supported catalyst and an organic solvent in a reaction vessel, introducing hydrogen to ensure that the pressure of the hydrogen in the reaction vessel is 0.1-2.0MPa, and stirring and reacting at 15-45 ℃ until the reaction is complete; filtering to remove the catalyst, adding purified water into the filtrate, cooling to 0-5 ℃, stirring, and precipitating 2-amino-5-thiophenyl- (2-methoxy) acetanilide crystals;the halogenated benzene is chlorobenzene or bromobenzene.
- 2. The method for producing 2-amino-5-phenylthio- (2-methoxy) acetanilide according to claim 1, wherein the mass ratio of the halogenated benzene to the 2-nitro-5-mercaptoaniline is 3.0 to 10.0, and the amount of the potassium carbonate is 0.5 to 3.0 times the molar amount of the 2-nitro-5-mercaptoaniline.
- 3. The method for producing 2-amino-5-phenylthio- (2-methoxy) acetanilide according to claim 1, wherein the mass ratio of methyl 2-methoxyacetate to 2-nitro-5-phenylthioaniline is 2.0 to 10.0, and the mass ratio of the alkane solvent to methyl 2-methoxyacetate is 1.0 to 5.0.
- 4. The method for preparing 2-amino-5-thiophenyl- (2-methoxy) acetanilide as claimed in claim 1, wherein said alkane solvent is one or more of C5-C8 alkane.
- 5. The method for preparing 2-amino-5-thiophenyl- (2-methoxy) acetanilide according to claim 4, wherein said alkane solvent is one or more selected from n-pentane, n-hexane, n-heptane and isooctane.
- 6. The method for preparing 2-amino-5-thiophenyl- (2-methoxy) acetanilide as claimed in claim 4, wherein said alkane solvent is one or a mixture of n-hexane and n-heptane.
- 7. The method for producing 2-amino-5-phenylthio- (2-methoxy) acetanilide according to claim 1, wherein the mass ratio of the organic solvent to the 2-nitro-5-phenylthio- (2-methoxy) acetanilide is 3.0 to 15.0, and the amount of the purified water is 0.1 to 1.0 times the mass of the organic solvent.
- 8. The method for preparing 2-amino-5-thiophenyl- (2-methoxy) acetanilide as claimed in claim 1, wherein said organic solvent is one or more of methanol, ethanol and propanol.
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| DE2548910A1 (en) * | 1975-10-31 | 1977-05-12 | Bayer Ag | (2)-Acylamino-nitro-benzene derivs. - which are intermediates for anthelmintic guanidine derivs. |
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| CN1308607A (en) * | 1998-07-01 | 2001-08-15 | 拜尔公司 | Method for preparing 2-nitro-5-(phenylthio)-anilines |
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| Title |
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| Preparation of dimethyl ester of N-[2-[(methoxyacetyl)amino]-4- (phenylthio)phenyl]carbonimidoyl-N,N’-biscarbamic acid;A. Skibinski,等;《Polish Journal of Applied Chemistry》;19951231;第39卷(第1期);91-94 * |
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