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Method for producing antitype-4-alkylthio cinnamic acid

A technology of cinnamic acid and alkylthio, applied in the field of preparation of trans-4-alkylthiocinnamic acid

Active Publication Date: 2011-01-19
SHANGHAI TIANCI INT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the good solubility of trans-4-mercaptocinnamic acid in alkaline aqueous solution, the one-pot synthesis of trans-4-alkylthiocinnamic acid under aqueous conditions has dual value in terms of economy and environment, domestic and foreign literature None reported

Method used

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  • Method for producing antitype-4-alkylthio cinnamic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) The preparation of trans-4-chlorosulfonyl cinnamic acid (II), its synthetic route is as follows:

[0036]

[0037] Chlorosulfonic acid (60 mL, 0.9 mol) was placed in a 250 mL round bottom flask and cooled to 0 °C with an ice bath. Cinnamic acid (14.8 g, 0.1 mol) was added to the flask in 8 portions over 1.5 hours. Control the reaction temperature at 0°C for 16 hours. The ice bath was removed, and the reaction solution naturally returned to room temperature, and then reacted in an oil bath at 55° C. for 0.8 hours, and the oil bath was removed again, and the reaction solution was naturally cooled to room temperature. The resulting brown-red reaction solution was slowly poured into 600 mL of ice water. Let stand, filter, wash the filter cake with ice water, recrystallize in 300mL glacial acetic acid, filter, and the filtrate is a white solid. P 2 o 5 After drying, white trans-4-chlorosulfonyl cinnamic acid (II) is obtained. Wherein the molar ratio of chlorosul...

Embodiment 2

[0046] (1) Preparation of trans-4-chlorosulfonyl cinnamic acid (II)

[0047] Chlorosulfonic acid (80 mL, 1.2 mol) was placed in a 250 mL round bottom flask and cooled to 0 °C with an ice bath. Cinnamic acid (14.8 g, 0.1 mol) was added to the flask in 10 portions over 2.5 hours. Control the reaction temperature at 0°C for 16 hours. The ice bath was removed, and the reaction liquid was naturally returned to room temperature, and then reacted in an oil bath at 55° C. for 1.2 hours, and the oil bath was removed again, and the reaction liquid was naturally cooled to room temperature. The resulting brown-red reaction solution was slowly poured into 600 mL of ice water. Let stand, filter, wash the filter cake with ice water, recrystallize in 300mL glacial acetic acid, filter, and the filtrate is a white solid. P 2 o 5 After drying, white trans-4-chlorosulfonyl cinnamic acid (II) was obtained. Wherein the molar ratio of chlorosulfonic acid and cinnamic acid is 12:1.

[0048] Th...

Embodiment 3

[0056] (1) Preparation of trans-4-chlorosulfonyl cinnamic acid (II)

[0057] Chlorosulfonic acid (66 mL, 1 mol) was placed in a 250 mL round bottom flask and cooled to 0 °C with an ice bath. Cinnamic acid (14.8 g, 0.1 mol) was added to the flask in 10 portions over 1.5 hours. Control the reaction temperature at 0°C for 18 hours. The ice bath was removed, and the reaction solution naturally returned to room temperature, and then reacted in an oil bath at 60° C. for 1 hour, and the oil bath was removed again, and the reaction solution was naturally cooled to room temperature. The resulting brown-red reaction solution was slowly poured into 600 mL of ice water. Let stand, filter, wash the filter cake with ice water, recrystallize in 300mL glacial acetic acid, filter, and the filtrate is a white solid. P 2 o 5 After drying, white trans-4-chlorosulfonyl cinnamic acid (II) is obtained. Wherein the molar ratio of chlorosulfonic acid and cinnamic acid is 10:1.

[0058] (2) The ...

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Abstract

The invention belongs to the field of synthesizing medicine intermediates, in particular to a preparation method for a trans-4-alkylthio cinnamic acid (I). The invention uses a cinnamic acid and a chlorosulfonic acid as raw materials to firstly prepare a trans-4- chlorosulfonyl chichi cinnamic acid, then uses a stannous chloride-acetic acid system reduction thrans-4-chlorosulfonyl cinnamic acid to get an unstable intermediate trans-4- mercapto cinnamic acid. The latter is not needed to be separated, which can be directly reacted with an aliphatic (alkyl) halogenated hydrocarbon in an alkalineaqueous liquid to synthesize the needed products. The trans-4-alkylthio cinnamic acid synthesized by the method is an important medicine synthesizing intermediate and can be used to synthesize natural products with physiological activity, which can obtain the cinnamic acid containing a sulfoxide group and a sulfonyl group through selective oxidation and is a valuable 'block' in organic chemistry synthesis. After the reaction with Hunsdiecker or the decarboxylation reaction by adding bromine, the trans-4-alkylthio cinnamic acid can also be converted to a Beta-brominated aromatic ethylene, which is widely applied to synthesize the selective stereo substituted olefins with the existence of metal catalytic reagent.

Description

Technical field [0001] The present invention is the field of drug intermediate synthesis, which involves a preparation method of a transfiguration-4-alkyl cinnamonic acid (i). Background technique [0002] Alkyl aromatherapy sulfe ether is an important synthetic intermediate in organic synthesis [1] , Widely used in the synthesis of hand -tadpoles and Yama [2] EssenceThey are also important types of compounds in biology and have important physiological functions.The reported typical preparation methods are mainly sulfur or sulfhenol salt under the action of strong alkali, and then a synthesis reaction with halogenic hydrocarbons to generate sulfur ether.Most of these methods are completed in organic solvents such as N, N-dimethylrmamide, dizomya, acetylene, isopropanol, or ethanol [3] EssenceAlthough there are reports that the reaction to generate sulfur ether in the water agglutination, organic solvents such as benzene are still needed as a common solvent [4] EssenceThere is on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/62C07C319/14
Inventor 匡春香张文生江玉波胡婷华
Owner SHANGHAI TIANCI INT PHARMA