CN113336679A - Synthesis method of triflusulfuron-methyl intermediate - Google Patents

Synthesis method of triflusulfuron-methyl intermediate Download PDF

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CN113336679A
CN113336679A CN202110633119.2A CN202110633119A CN113336679A CN 113336679 A CN113336679 A CN 113336679A CN 202110633119 A CN202110633119 A CN 202110633119A CN 113336679 A CN113336679 A CN 113336679A
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chlorphenyl
triflusulfuron
reducing agent
trifluoropropyl
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杨传鹏
邹佩佩
陈新
祝丹
孙永辉
孔繁蕾
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Jiangsu Agrochem Laboratory Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups

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Abstract

The invention discloses a synthesis method of 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide as an intermediate of fluosulfuron, which is prepared by using o-chlorobenzonitrile and ethyl trifluoroacetate as starting raw materials, performing acylation reaction in the presence of organic base, performing decyanation reaction in the presence of sulfuric acid, performing reduction reaction in the presence of a reducing agent, performing dehydration reaction in the presence of a catalyst, performing reduction reaction in the presence of a reducing agent, performing sulfhydrylation reaction with a sulfhydrylation reagent, performing sulfonylchlorination reaction with chlorine in the presence of water, and performing sulfonylamination reaction with ammonia water. Compared with the prior art, the synthesis method has the advantages of cheap and easily-obtained raw materials and auxiliary agents, mild reaction conditions, simple and convenient operation, higher safety and more environmental friendliness, is especially important in the current times with stricter requirements on safety and environmental protection, and can ensure the safety of industrial production.

Description

Synthesis method of triflusulfuron-methyl intermediate
Technical Field
The invention belongs to the technical field of herbicide intermediate synthesis, and particularly relates to a synthetic method of a triflusulfuron-methyl intermediate 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide.
Background
Triflusulfuron-methyl is a sulfonylurea herbicide, which is suitable for crops such as corn, sorghum, cereal crops, lawns and pastures. The half-life period of the triflusulfuron-methyl in soil is 8-40d, the half-life period in corn plants is l-2.5h, and the half-life period is obviously shorter than the metabolism time of other commercial sulfonylurea herbicides in the corn plants, so that the florusulfuron-methyl is safer.
2- (3, 3, 3-trifluoropropyl) benzenesulfonamide is an important intermediate for synthesizing triflusulfuron.
Chinese patent document CN1083480A discloses a preparation method of 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide, which takes o-aminobenzenesulfonic acid as a starting material and is firstly processed by weightNitriding, then Pd (dba)2Reacting with 3,3, 3-trifluoropropene under catalysis to obtain sodium 2- (3, 3, 3-trifluoropropene) benzenesulfonate; then carrying out catalytic hydrogenation to obtain 2- (3, 3, 3-trifluoropropyl) sodium benzenesulfonate; and finally reacting with phosgene and ammonia water to obtain the 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide.
The reaction formula is as follows:
Figure DEST_PATH_IMAGE001
。
the disadvantages of this method are: (1) 3,3, 3-trifluoropropene serving as a raw material is difficult to transport and store, so that the industrial operation is difficult; (2) catalyst Pd (dba)2The price is high, so that the production cost is high; (3) phosgene is a highly toxic product, has poor safety and is extremely unfriendly to the environment.
Disclosure of Invention
The invention aims to solve the problems and provides a synthetic method of a triflusulfuron-methyl intermediate, which has the advantages of cheap and easily-obtained raw materials and auxiliary agents, mild reaction conditions, higher safety, environmental friendliness and suitability for industrial production.
The technical scheme for realizing the purpose of the invention is as follows: a synthetic method of a triflusulfuron-methyl intermediate comprises the following steps:
carrying out acylation reaction on o-chlorobenzene acetonitrile and ethyl trifluoroacetate serving as starting raw materials in the presence of organic alkali to obtain 2- (2-chlorphenyl) -3-ketone-4, 4, 4-trifluorobutyronitrile;
carrying out decyanation reaction on the 2- (2-chlorphenyl) -3-ketone-4, 4, 4-trifluorobutyronitrile obtained in the step I in the presence of sulfuric acid to obtain 1,1, 1-trifluoro-2-ketone-3- (2-chlorphenyl) propane;
carrying out reduction reaction on the 1,1, 1-trifluoro-2-ketone-3- (2-chlorphenyl) propane obtained in the step (II) in the presence of a reducing agent to obtain 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorphenyl) propane;
fourthly, the 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorphenyl) propane obtained in the third step is subjected to dehydration reaction in the presence of a catalyst to obtain 1- (2-chlorphenyl) -3,3, 3-trifluoropropene;
fifthly, the 1- (2-chlorphenyl) -3,3, 3-trifluoropropene obtained in the step (iv) is subjected to reduction reaction in the presence of a reducing agent to obtain 1- (2-chlorphenyl) -3,3, 3-trifluoropropane;
sixthly, carrying out sulfhydrylation reaction on the obtained 1- (2-chlorphenyl) -3,3, 3-trifluoropropane and sulfhydrylation reagent to obtain 2- (3, 3, 3-trifluoropropyl) thiophenol;
seventhly, carrying out sulfonyl chlorination reaction on the obtained 2- (3, 3, 3-trifluoropropyl) thiophenol and chlorine in the presence of water to obtain 2- (3, 3, 3-trifluoropropyl) benzenesulfonyl chloride, and carrying out sulfonamide reaction on the obtained 2- (3, 3, 3-trifluoropropyl) benzenesulfonyl chloride and ammonia water to obtain the fluosulfuron-methyl intermediate 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide.
In the step I, the molar ratio of the o-chlorobenzonitrile to the ethyl trifluoroacetate is 1: 1-1: 2, and preferably 1: 1-1: 1.5.
In the above step (i), the acylation reaction is carried out in an alcohol solvent, and the alcohol solvent is preferably ethanol.
In the step I, the mol ratio of the o-chlorobenzene acetonitrile to the organic alkali is 1: 0.8-1: 1.5.
In the step (i), the organic base is one of sodium ethoxide, sodium methoxide and sodium tert-butoxide, and preferably sodium ethoxide.
In the step I, the acylation reaction temperature is 60-80 ℃.
In the second step, the concentration of the sulfuric acid is 50-80 wt%.
In the second step, the temperature of the decyanation reaction is the reflux temperature.
In the third step, the reduction reaction is performed in an alcohol solvent, and the alcohol solvent is preferably methanol.
In the third step, the molar ratio of the 1,1, 1-trifluoro-2-one-3- (2-chlorophenyl) propane to the reducing agent is 1: 1-1: 4, preferably 1: 1.5-1: 2.5.
In the third step, the reducing agent is sodium borohydride.
In the third step, the reduction reaction temperature is room temperature (20-30 ℃, the same applies below).
In the above-mentioned step (iv), the dehydration reaction is carried out in a benzene-based solvent, and the benzene-based solvent is preferably toluene.
In the step (iv), the molar ratio of the 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorophenyl) propane to the catalyst is 1: 1 to 1: 4, preferably 1: 2 to 1: 3.
In the step (iv), the catalyst is phosphorus oxychloride or phosphorus pentachloride.
In the above-mentioned step (iv), the dehydration reaction temperature is a reflux temperature.
In the above fifth step, the reduction reaction is performed in an alcohol solvent, and the alcohol solvent is preferably methanol.
In the fifth step, the mol ratio of the 1- (2-chlorphenyl) -3,3, 3-trifluoropropene to the reducing agent is 1: 1-1: 4, preferably 1: 1.5-1: 2.5.
In the fifth step, the reducing agent is sodium borohydride.
In the fifth step, the reduction reaction temperature is room temperature.
In the above step, the thiolation is performed in a polar organic solvent, preferably DMF.
In the step (c), the molar ratio of the 1- (2-chlorphenyl) -3,3, 3-trifluoropropane to the sulfhydrylation reagent is 1: 1-1: 2.
In the step (sixthly), the sulfhydrylation reagent is sodium hydrosulfide or benzyl mercaptan.
In the step, the temperature of the sulfhydrylation reaction is 50-75 ℃.
In the above step (c), the sulfonyl chloride reaction is carried out in a halogenated hydrocarbon solvent, preferably dichloromethane.
The synthetic route is as follows:
Figure DEST_PATH_IMAGE003
。
the invention has the following positive effects: compared with the prior art, the synthesis method has the advantages of cheap and easily-obtained raw materials and auxiliary agents, mild reaction conditions, simple and convenient operation, higher safety and more environmental friendliness, is especially important in the current times with stricter requirements on safety and environmental protection, and can ensure the safety of industrial production.
Detailed Description
(example 1)
This example is a preparation of 2- (2-chlorophenyl) -3-keto-4, 4, 4-trifluorobutyronitrile, as follows:
adding 15.1g of o-chlorobenzonitrile (0.1 mol) and 50g of ethanol into a reaction device, then adding 17.0g of trifluoroacetyl ethyl ester (0.12 mol, 1.2 eq), then dropwise adding 34.5g of sodium ethoxide solution (0.1 mol, 1 eq) with the concentration of 20wt% at the temperature of 25-30 ℃, and heating to 70-75 ℃ after dropwise adding for reaction for 5 hours.
After the reaction, ethanol was distilled off, 50g of water was added, hydrochloric acid was added dropwise to adjust the pH to acidity, and a solid was precipitated, which was then filtered and dried to obtain 21.8g of 2- (2-chlorophenyl) -3-keto-4, 4, 4-trifluorobutyronitrile as a white solid powder with a yield of 88.4% and a purity of 93.5% (HPLC).
(example 2)
This example is a preparation of 1,1, 1-trifluoro-2-one-3- (2-chlorophenyl) propane, as follows:
50g of 60wt% sulfuric acid (0.3 mol) is added into a reaction device, 10.0g of 2- (2-chlorophenyl) -3-keto-4, 4, 4-trifluorobutyronitrile (0.04 mol) is added under stirring, and the mixture is heated to reflux for reaction for 3 hours.
After the completion of the reaction, the distillate was subjected to distillation, and the distillate was washed with 20g of water to give 8.1g of 1,1, 1-trifluoro-2-one-3- (2-chlorophenyl) propane as a pale yellow oily liquid in a yield of 90.1% and a purity of 95.5% (HPGC).
(example 3)
This example is a preparation of 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorophenyl) propane, as follows:
11.1g of 1,1, 1-trifluoro-2-one-3- (2-chlorophenyl) propane (0.05 mol) and 50g of methanol were charged into a reaction apparatus, and then 4.0g of sodium borohydride (0.105 mol, 2.1 eq) was added in portions at a temperature of 25 ℃ and the reaction was kept at that temperature for 2 hours.
After the reaction, the reaction mixture was filtered by suction, and the filtrate was evaporated to dryness to obtain 10.5g of 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorophenyl) propane as a pale yellow oily liquid, with a yield of 93.8% and a purity of 93.8% (HPGC).
(example 4)
This example is a preparation of 1- (2-chlorophenyl) -3,3, 3-trifluoropropene, as follows:
11.2g of 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorophenyl) propane (0.05 mol) and 40g of toluene were charged into a reaction apparatus, 20.0g of phosphorus oxychloride (0.13 mol, 2.6 eq) was added with stirring, and the mixture was heated to reflux for 5 hours.
After the reaction, the temperature was reduced to 20 ℃, the reaction solution was added dropwise to water, the liquid was separated, the aqueous phase was extracted once with toluene, the organic layers were combined, washed with water and evaporated to dryness to obtain 9.2g of 1- (2-chlorophenyl) -3,3, 3-trifluoropropene as a pale yellow liquid with a yield of 89.3% and a purity of 96.2% (HPGC).
(example 5)
This example is a preparation of 1- (2-chlorophenyl) -3,3, 3-trifluoropropane, as follows:
10.3g of 1- (2-chlorophenyl) -3,3, 3-trifluoropropene (0.05 mol) and 50g of methanol were charged into the reaction apparatus, and then 3.8g of sodium borohydride (0.1 mol, 2 eq) was added at a temperature of 25 ℃ to complete the reaction for 3 hours while maintaining the temperature.
After the reaction, the reaction mixture was filtered by suction, and the filtrate was evaporated to dryness to obtain 9.5g of 1- (2-chlorophenyl) -3,3, 3-trifluoropropane as a pale yellow liquid in a yield of 91.3% and a purity of 95.3% (HPGC).
(example 6)
This example is a preparation of 2- (3, 3, 3-trifluoropropyl) thiophenol, as follows:
45g of DMF was charged into the reactor, 10.4g of 1- (2-chlorophenyl) -3,3, 3-trifluoropropane (0.05 mol) and 3.6g of sodium hydrosulfide (0.064 mol, 1.3 eq) were added thereto, and the mixture was heated to 60 ℃ to react for 6 hours.
After the reaction was completed, DMF was evaporated under reduced pressure, 50g of water was added, extraction was performed twice with dichloromethane, the organic phases were combined, washed with water and evaporated to dryness to obtain 9.4g of 2- (3, 3, 3-trifluoropropyl) thiophenol as a yellow oily liquid, with a yield of 91.5% and a purity of 98.2% (HPGC).
(example 7)
This example is a preparation of a target product, 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide, as follows:
10.0g of 2- (3, 3, 3-trifluoropropyl) thiophenol (0.0485 mol), 50g of dichloromethane and 25g of water were added to a reaction apparatus, the temperature was reduced to 0 ℃ and chlorine gas was introduced to the reaction apparatus to react for 1 hour.
After the reaction is finished, the liquid is separated, the water phase is extracted once by 25g of dichloromethane, the organic phases are combined and added into another reaction device, the temperature is reduced to 0 ℃, 10.5g of ammonia water is added dropwise, and the reaction is carried out for 1 hour.
After the reaction, hydrochloric acid was added dropwise to adjust the pH to acidity, followed by suction filtration to obtain 10.8g of 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide as a white solid, in a yield of 87.9% and a purity of 93.7% (HPLC).

Claims (8)

1. A synthetic method of a triflusulfuron-methyl intermediate comprises the following steps:
carrying out acylation reaction on o-chlorobenzene acetonitrile and ethyl trifluoroacetate serving as starting raw materials in the presence of organic alkali to obtain 2- (2-chlorphenyl) -3-ketone-4, 4, 4-trifluorobutyronitrile;
carrying out decyanation reaction on the 2- (2-chlorphenyl) -3-ketone-4, 4, 4-trifluorobutyronitrile obtained in the step I in the presence of sulfuric acid to obtain 1,1, 1-trifluoro-2-ketone-3- (2-chlorphenyl) propane;
carrying out reduction reaction on the 1,1, 1-trifluoro-2-ketone-3- (2-chlorphenyl) propane obtained in the step (II) in the presence of a reducing agent to obtain 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorphenyl) propane;
fourthly, the 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorphenyl) propane obtained in the third step is subjected to dehydration reaction in the presence of a catalyst to obtain 1- (2-chlorphenyl) -3,3, 3-trifluoropropene;
fifthly, the 1- (2-chlorphenyl) -3,3, 3-trifluoropropene obtained in the step (iv) is subjected to reduction reaction in the presence of a reducing agent to obtain 1- (2-chlorphenyl) -3,3, 3-trifluoropropane;
sixthly, carrying out sulfhydrylation reaction on the obtained 1- (2-chlorphenyl) -3,3, 3-trifluoropropane and sulfhydrylation reagent to obtain 2- (3, 3, 3-trifluoropropyl) thiophenol;
seventhly, carrying out sulfonyl chlorination reaction on the obtained 2- (3, 3, 3-trifluoropropyl) thiophenol and chlorine in the presence of water to obtain 2- (3, 3, 3-trifluoropropyl) benzenesulfonyl chloride, and carrying out sulfonamide reaction on the obtained 2- (3, 3, 3-trifluoropropyl) benzenesulfonyl chloride and ammonia water to obtain the fluosulfuron-methyl intermediate 2- (3, 3, 3-trifluoropropyl) benzenesulfonamide.
2. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the first step, the organic base is one of sodium ethoxide, sodium methoxide and sodium tert-butoxide; the mol ratio of the o-chlorobenzonitrile to the organic base is 1: 0.8-1: 1.5; the acylation reaction temperature is 60-80 ℃.
3. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the second step, the concentration of the sulfuric acid is 50-80 wt%, and the temperature of the decyanation reaction is the reflux temperature.
4. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the third step, the molar ratio of the 1,1, 1-trifluoro-2-one-3- (2-chlorophenyl) propane to the reducing agent is 1: 1-1: 4, the reducing agent is sodium borohydride, and the reduction reaction temperature is room temperature.
5. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the step (iv), the molar ratio of the 1,1, 1-trifluoro-2-hydroxy-3- (2-chlorophenyl) propane to the catalyst is 1: 1-1: 4, the catalyst is phosphorus oxychloride or phosphorus pentachloride, and the dehydration reaction temperature is reflux temperature.
6. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the fifth step, the molar ratio of the 1- (2-chlorophenyl) -3,3, 3-trifluoropropene to the reducing agent is 1: 1-1: 4, the reducing agent is sodium borohydride, and the reduction reaction temperature is room temperature.
7. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the step (c), the molar ratio of the 1- (2-chlorophenyl) -3,3, 3-trifluoropropane to the sulfhydrylation reagent is 1: 1-1: 2, the sulfhydrylation reagent is sodium hydrosulfide or benzylmercaptan, and the sulfhydrylation reaction temperature is 50-75 ℃.
8. The method for synthesizing a triflusulfuron-methyl intermediate according to claim 1, characterized in that: in the above step (c), the sulfonyl chloride reaction is performed in a halogenated hydrocarbon solvent, and the halogenated hydrocarbon solvent is dichloromethane.
CN202110633119.2A 2021-06-07 2021-06-07 Synthesis method of triflusulfuron-methyl intermediate Withdrawn CN113336679A (en)

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Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
W. CARRUTHERS: "《现代有机合成方法》", 30 April 1990, 青岛海洋大学出版社 *
刘鹰翔: "《药物合成反应》", 31 August 2017, 中国中医药出版社 *
郭峰 等: "邻溴苯磺酰氯的合成", 《化学试剂》 *

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