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Preparation of 2-aryl-5-(trifluoride) pyrrole-3-nitrile and its use and preparation of its intermediate thereof

A trifluoromethyl and aryl technology, applied in the field of preparation of intermediates, can solve the problems of unsatisfactory effectiveness and economic efficiency, and achieve the effects of low cost, high yield and simple process

Inactive Publication Date: 2003-09-03
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many patented methods for the preparation of such compounds and related intermediates, but they are not yet ideal in terms of effectiveness and economy

Method used

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Examples

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preparation example Construction

[0018] Currently known methods for preparing α-aryl trifluoroacetyl amino acids of formula (II) use trifluoroacetic anhydride or ethyl trifluoroacetate as trifluoroacetylating reagents (US 5118816, CN1035669C, etc.). U.S. Patent No. 5,144,041 discloses that α-aryl trifluoroacetylamino acid (wherein A is some substituting group except hydrogen) similar to formula (II) reacts with 2-halogenated acrylonitrile in the presence of acid anhydride, organic base and solvent The reaction is analogous to the method for preparing 2-aryl-5-(trifluoromethyl)pyrrole-3-carbonitrile compounds of formula III wherein A is some substituent other than hydrogen.

[0019] In the present invention, the α-aryl amino acid of formula (I) can be directly used for trifluoroacetylation with trifluoroacetic acid and acyl chloride reagent, and the yield is good. Advantageously, the method of the present invention does not need to use expensive trifluoroacetic anhydride, does not use ethyl trifluoroacetate wi...

Embodiment 1

[0028] The preparation of embodiment 1α-(p-chlorophenyl)-N-(trifluoroacetyl) glycine

[0029] A mixture of α-(p-chlorophenyl)glycine (5.6g, 0.03mol) in acetonitrile was treated successively with trifluoroacetic acid (4.8g, 0.042mol) and phosphorus trichloride (1.8g, 0.013mol) at reflux Stir at high temperature for 5-6 hours, followed by HPLC analysis until the complete conversion of α-(p-chlorophenyl)glycine. The reaction mixture was cooled and concentrated in vacuo to give a light yellow solid residue. The solid residue was stirred with a water / toluene mixture, filtered and dried to obtain 5.2 g of the title product as a slightly yellowish white solid powder (yield 61.6%), mp: 170-172°C.

[0030] 1 H NMR (DMSO, δ): 5.49 (d, J = 7.4, 1H, C-H), 7.43 (m, 4H, Ar-H), 10.12 (bs, 1H, COO-H), 13.2 (bs, 1H, N-H ).

Embodiment 2

[0031] The preparation of embodiment 2α-(p-chlorophenyl)-N-(trifluoroacetyl) glycine

[0032] Using substantially the same method as described in Example 1 and substituting trichloromethyl chloroformate (3.6 g, 0.018 mol) for phosphorus trichloride therein as the acid chloride reagent, 5.9 g of the title product of light yellow solid powder (produced Rate 69.8%), mp: 177-170°C.

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Abstract

A process for preparing 2-aryl-5-(trifluoromethyl) pyrrole-3-nitrile includes such steps as reacting of alpha-arylamino acid on trifluoroacetic acid and acylchlorating reagent under existance of organic solvent to obtain the trifluoroacetyl derivative of alpha-arylamino acid, and reacting on 2-haloacrylonitrile under existance of alkali, organic solvent, and acylchlorating reagent or acid anhydride. Said alpha-aryl trifluoroacetylamino acid compound is prepared from trifluoroacetic acid and acylchlorating reagent through acetylation under existance of organic solvent.

Description

technical field [0001] The present invention relates to the preparation method of 2-aryl-5-(trifluoromethyl)pyrrole-3-carbonitrile and its application and be used for preparing 2-aryl-5-(trifluoromethyl)pyrrole-3-carbonitrile The preparation method of the intermediate. Background technique [0002] Arylpyrrolecarbonitriles and their derivatives are effective insecticides, acaricides and molluscicides, especially 2-aryl-5-(trifluoromethyl)pyrrole-3-carbonitriles and their derivatives are highly efficient and broad-spectrum, such as 4-Bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile, namely chlorfenapyr, developed by American cyanamide company Insecticides and acaricides have been on the market for many years. There are many patented methods for the preparation of such compounds and related intermediates, but they are not yet ideal in terms of effectiveness and economy. Contents of the invention [0003] The object of the present inventi...

Claims

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Application Information

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IPC IPC(8): C07D207/416
Inventor 徐尚成万琴俞幼芬王晓军许志专
Owner JIANGSU PESTICIDE RES INST
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