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CN114213294B - Method for synthesizing disulfide compound by using basic zeolite molecular sieve as catalyst - Google Patents

Method for synthesizing disulfide compound by using basic zeolite molecular sieve as catalyst Download PDF

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CN114213294B
CN114213294B CN202111613758.9A CN202111613758A CN114213294B CN 114213294 B CN114213294 B CN 114213294B CN 202111613758 A CN202111613758 A CN 202111613758A CN 114213294 B CN114213294 B CN 114213294B
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catalyst
synthesizing
disulfide
nitrogen atmosphere
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CN114213294A (en
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唐天地
孟从玮
朱超杰
刘会丽
傅雯倩
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Changzhou University
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C07C319/24Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/70Sulfur atoms
    • C07D213/71Sulfur atoms to which a second hetero atom is attached
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30Hetero atoms other than halogen
    • C07D333/34Sulfur atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The invention discloses a method for catalyzing and synthesizing disulfide compounds by using an alkaline zeolite molecular sieve, belonging to the field of green organic fine catalytic synthesis. According to the method for synthesizing the disulfide compound by using the thiol compound as the substrate, the aromatic thiol, the aliphatic thiol and the heterocyclic thiol are subjected to self-coupling reaction under the condition of no oxidant and no metal in the nitrogen atmosphere through the solid base catalysis of the ETS-10 zeolite molecular sieve, and the sulfur hydrogen bond is activated. Finally obtaining a series of disulfide compounds. The method has simple steps, high product yield and easy separation and purification.

Description

Method for synthesizing disulfide compound by using basic zeolite molecular sieve as catalyst
Technical Field
The invention belongs to the field of green organic fine catalytic synthesis, and particularly relates to a method for synthesizing disulfide compounds by catalyzing mercaptan compounds with an ETS-10 zeolite molecular sieve.
Background
In natural compounds, biological agents and drugs, the sulfur-sulfur bond is a functional group which has high value and rich content, and shows excellent biological activity and reaction activity. Because of their biocompatibility, disulfide compounds have been used by drug researchers as important intermediates in the synthesis of new drugs, as well as precursors for drug delivery. In addition, the disulfide compound plays an important role in functional materials such as biological materials, biochemical sensors, rechargeable batteries, rubber vulcanization accelerators and the like.
General methods for synthesizing disulfide compounds include a thiolation method, a reductive dimerization method of a thiolate, a reductive coupling method of sulfur or polysulfide substituted alkyl halohydrocarbon, a sulfonyl chloride, and the like, and in the above-described method for synthesizing disulfide compounds, thiol is oxidized with a strong oxidizing agent to form a corresponding radical, and then disulfide compounds are formed. In industry, the production of disulfide compounds generally uses only equivalent amounts of oxidizing agents, such as NaClO or NaNO 2, for oxidative coupling reactions (j. Chem. Technology. Biotechnol.,2012,87,341-345). However, during the reaction, harmful liquid wastes are generated, which contain a large amount of salts and nitrogen oxides, so that the treatment cost increases and the environment is not friendly. Accordingly, other catalysts using oxygen as an oxidizing agent are also produced, such as metal salts K 3PO4 (Tetrahedron letters 2005,46,3583), csF (Tetrahedron letters 2003,44,6789), metal oxides CeO 2 (chem. Sci.2012,3,398), transition metals (Green chem.,2017,19,2491-2495), organic ligand catalysts (Asian j. Org. Chem.,2017,6,265-268), enzymes (Green chem.,2013,15,1490-1495), etc., but when asymmetric coupling reactions of thiols are catalyzed by these catalysts, not only yields are low, but also are not easily separable, and are liable to affect subsequent processes.
The titanosilicate molecular sieve ETS-10 is formed by bridging SiO 4 tetrahedron and TiO 6 octahedron through sharing oxygen atoms, and simultaneously has a three-dimensional pore canal structure of a three-membered ring, a five-membered ring, a seven-membered ring and a twelve-membered ring. The SiO 4 tetrahedron in the framework is electrically neutral, and the whole octahedron has 2 negative charges due to the fact that Ti is positioned in the center of the TiO 6 octahedron. This allows ETS-10 to have a stronger Lewis base. Thus, ETS-10 may be used in a base catalyzed reaction. We have found through research that the basic sites on the ETS-10 surface are capable of adsorbing and activating thiol compounds, converting them into the corresponding free radicals, and generating disulfide compounds through free radical coupling reactions.
Therefore, the invention provides a one-step method for converting the mercaptan compound into the disulfide compound by taking alkaline ETS-10 as a catalyst without using a traditional metal catalyst and a strong oxidant, and the method is high-efficiency and clean, has no byproduct generation, has high atom economy, and is easy to separate and recycle the catalyst.
Disclosure of Invention
The invention uses commercial basic ETS-10 zeolite as a catalyst, and realizes the direct conversion of the mercaptan compound into the disulfide compound in a nitrogen atmosphere under the condition of not using a strong oxidant or metal salt.
The specific synthesis method is as follows:
the preparation method comprises the steps of taking a mercaptan compound as a reaction raw material, adding a set amount of ETS-10 zeolite as a catalyst into a reaction tube, adding a solvent, reacting in a nitrogen atmosphere, centrifuging to obtain a reaction liquid, and performing column chromatography separation on the obtained liquid product after rotary evaporation to obtain the disulfide compound.
Wherein the mercaptan compound is aromatic mercaptan, heterocyclic mercaptan and aliphatic mercaptan, and the structural formulas are shown in formula I, formula II and formula III respectively:
Further, the catalyst used in the present invention is a nano ETS-10 zeolite catalyst.
Further, the organic solvent selected for the reaction is selected from one of dichloromethane, dimethyl sulfoxide and cyclohexane.
Further, the amount of the thiol organic compound to be added is 0.005 to 0.02:1 (mol/g) relative to the amount of the catalyst.
Further, the reaction temperature is 80-120 ℃ and the reaction time is 3-10 h.
Compared with the prior art, the invention has the following technical advantages
(1) Compared with the catalytic reaction system of metal salts (K 3PO4, csF) and metal oxides (CeO 2) reported in the literature, the catalytic reaction system can realize the reaction under the nitrogen atmosphere, and does not need to add an additional strong oxidant or oxygen.
(2) The invention has high tolerance of functional groups, wide substrate range, low toxicity, environmental friendliness and simple synthesis method, and the selectivity of the disulfide compounds reaches 100 percent, and the subsequent separation steps are also simple.
Drawings
FIG. 1 is a chart showing the NMR spectrum of dibenzyldisulfide 1 H of example 1
FIG. 2 is a chart showing the NMR spectrum of bis (2-aminophenyl) disulfide 1 H of example 2
FIG. 3 is a chart showing the NMR spectrum of p-toluenedisulfide 1 H of example 3
FIG. 4 is a chart showing the NMR spectrum of p-methoxydisulfide 1 H of example 4
FIG. 5 is a chart showing the NMR spectrum of p-bromophenyl sulfide 1 H of example 5
FIG. 6 is a chart of the NMR spectrum of dicyclohexyl disulfide 1 H of example 6
FIG. 7 is a chart showing the NMR spectrum of bis (2-thienyl) disulfide 1 H
FIG. 8 is a chart showing the NMR spectrum of dimethyl 3,3' -dithiodipropionate 1 H
FIG. 9 is a 1 H NMR spectrum of p-chlorobenzyl sulfide of example 9
FIG. 10 is a chart showing the NMR spectrum of bis (2-pyridyl) disulfide 1 H of example 10
Detailed Description
For a further understanding of the objects, aspects and advantages of the present invention, specific embodiments of the present invention will now be described in detail, but are not limited to the examples described below, and the reaction conditions will be changed according to the actual circumstances.
Example 1:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. After rotary evaporation, the obtained liquid phase product was subjected to flash column chromatography (volume ratio of petroleum ether and ethyl acetate as eluent: 10:1) to obtain a yellow oily substance. The yield of the product can reach 95%, and the characterization data of the product are as follows: 1 H NMR (500 MHz, chloro form-d) delta 7.25-7.12 (m, 10H), 3.50 (s, 4H).
Example 2:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of o-aminothiophenol and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The solid phase product obtained was subjected to flash column chromatography (eluting reagent petroleum ether to ethyl acetate in a volume ratio of 4:1) to give a yellow solid. The yield of the product can reach 90%, and the characterization data of the product are as follows :1H NMR(500MHz,Chloroform-d)δ7.09(ddd,J=7.6,6.1,1.8Hz,4H),6.66–6.62(m,2H),6.54–6.49(m,2H),4.26(s,4H).
Example 3:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of p-methylthiophenol and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The solid phase product obtained was subjected to flash column chromatography (volume ratio of petroleum ether to ethyl acetate as eluent: 50:1) to obtain a white solid. The yield of the product can reach 84%, and the characterization data of the product are as follows: 1 H NMR (500 mhz, chloroform-d) delta 7.30 (d, j=8.2 hz, 5H), 7.02 (d, j=7.9 hz, 5H), 2.23 (s, 6H).
Example 4:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of p-methoxyphenylthiophenol and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The solid phase product obtained was subjected to flash column chromatography (volume ratio of petroleum ether to ethyl acetate as eluent: 10:1) by rotary evaporation to give pale yellow liquid. The product yield can reach 89%, and the characterization data of the product are as follows: 1 H NMR (500 mhz, chloro-d) delta 7.32 (d, j=8.9 hz, 4H), 6.76 (d, j=8.8 hz, 4H), 3.72 (s, 6H).
Example 5:
30mg ETS-10 catalyst was weighed into the reaction tube, and then 0.22mmol of p-bromophenylthiophenol and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The solid phase product obtained was subjected to flash column chromatography (eluting with pure cyclohexane) by rotary evaporation to give a white solid. The product yield can reach 89%, and the characterization data of the product are as follows: 1 H NMR (500 MHz,Chloroform-d) delta 7.38-7.32 (m, 4H), 7.25 (d, j=8.6 hz, 4H).
Example 6:
30mg ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of cyclohexanediol and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The liquid phase product obtained was subjected to flash column chromatography (volume ratio of petroleum ether to ethyl acetate as eluent: 2:1) to obtain colorless liquid. The yield of the product can reach 89%, and the characterization data of the product are as follows :1H NMR(500 MHz,Chloroform-d)δ2.65–2.58(m,2H),2.02–1.95(m,4H),1.71(dd,J=9.4,4.6 Hz,4H),1.55(dt,J=10.3,3.4 Hz,2H),1.27–1.18(m,10H).
Example 7:
30 mg ETS-10 catalyst was weighed into the reaction tube, and then 0.2. 0.2 mmol of 2-thiophenol and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. Rotary evaporation to obtain liquid phase product, adding ethyl acetate, directly rotary evaporating to obtain product as yellow solid. The yield of the product can reach 98 percent, and the characterization data of the product are as follows :1H NMR(500 MHz,Chloroform-d)δ7.41(dd,J=5.3,1.3 Hz,2H),7.07(dd,J=3.6,1.3 Hz,2H),6.93(dd,J=5.3,3.6 Hz,2H).
Example 8:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of methyl 3-mercaptopropionate and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The liquid phase product obtained was subjected to flash column chromatography (volume ratio of petroleum ether to ethyl acetate as eluent: 50:1). The product yield can reach 82%, the obtained product is colorless oily liquid, and the characterization data of the product are as follows: 1 H NMR (500 MHz, chloro-d) delta 3.63 (s, 6H), 2.85 (s, 4H), 2.67 (s, 4H).
Example 9:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of 4-chlorobenzyl mercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The liquid phase product obtained was subjected to flash column chromatography (eluent petroleum ether and ethyl acetate in a volume ratio of 20:1) by rotary evaporation. The product yield was up to 90% and was a pale yellow oily liquid, the characterization data of the product were as follows: 1 H NMR (500 MHz, chloroform-d) delta 7.23-7.20 (m, 4H), 7.09-7.06 (m, 4H), 3.49 (s, 4H).
Example 10:
30mg of ETS-10 catalyst was weighed into the reaction tube, and then 0.2mmol of 2-mercaptopyridine and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The liquid phase product obtained was subjected to flash column chromatography (eluent petroleum ether and ethyl acetate in a volume ratio of 20:1) by rotary evaporation. The yield of the product was 92% and was a pale yellow oily liquid, and the characterization data of the product were as follows :1H NMR(500MHz,Chloroform-d)δ8.47(dd,J=4.9,2.0Hz,2H),7.55(td,J=7.7,2.0Hz,2H),7.39–7.36(m,2H),7.09(ddd,J=7.6,4.9,1.1Hz,2H).
Comparative example 1:
30mg of potassium fluoride catalyst was weighed into a reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 2:
30mg of potassium bromide catalyst was weighed into the reaction tube, followed by addition of 0.2mmol of benzylmercaptan and 1mL of cyclohexane. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 3:
30mg of potassium carbonate catalyst was weighed into a reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 4:
30mg of sodium carbonate catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 5:
30mg of sodium nitrate catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 6:
30mg of potassium nitrate catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 7:
30mg of rubidium nitrate catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 8:
30mg of cesium carbonate catalyst was weighed into a reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 9:
30mg of NaX catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
Comparative example 10:
30mg of NaY catalyst was weighed into the reaction tube, and then 0.2mmol of benzylmercaptan and 1mL of cyclohexane were added. And (3) reacting for 5 hours in a heater at 120 ℃ under the nitrogen atmosphere, and centrifuging after the experiment is finished. The obtained liquid phase was analyzed in Agilent gas chromatography to calculate the conversion of benzyl mercaptan and the selectivity of the target product.
(1) Compared with the traditional catalytic reaction system of the metal salt (K 3PO4, csF) and metal oxide (CeCO 2,Al2O3) catalytic reaction body, the invention can realize the reaction in the nitrogen atmosphere without adding additional strong oxidant
Catalyst Conversion% Selectivity%
Example 1 ETS-10 95 100
Comparative example 1 KF 3 100
Comparative example 2 KBr 5 100
Comparative example 3 K2CO3 trace(<1%) 100
Comparative example 4 Na2CO3 - -
Comparative example 5 NaNO3 - -
Comparative example 6 KNO3 - -
Comparative example 7 RbNO3 - -
Comparative example 8 Cs2CO3 trace(<1%) 100
Comparative example 9 NaX 30 65
Comparative example 10 NaY trace 100

Claims (5)

1. A method for synthesizing disulfide compounds, which is characterized by comprising the following steps: in nitrogen atmosphere, sequentially adding ETS-10 zeolite, mercaptan compounds and organic solvent into reaction equipment, reacting at a reaction temperature, centrifuging to obtain reaction liquid, and performing column chromatography separation on the obtained liquid product after rotary evaporation to obtain disulfide compounds.
2. The method for synthesizing the disulfide compound according to claim 1, wherein the structural formula of the thiol compound is shown as formula I, formula II and formula III respectively:
3. the method for synthesizing disulfide-based compounds according to claim 1, wherein the organic solvent is selected from one of dichloromethane, dimethyl sulfoxide and cyclohexane.
4. The method for synthesizing a disulfide compound according to claim 1, wherein the amount of the thiol compound to be added is 0.005 to 0.02:1 (mol/g) with respect to the amount of the catalyst.
5. The method for synthesizing disulfide compound according to claim 1, wherein the reaction temperature is 80-120 ℃ and the reaction time is 3-10 h.
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