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Method for producing 3,4-dichloro-n-(2-cyano-phenyl)-5-isothiazole carboxamide

A technology for isothiazole carboxamide and dimethylformamide is applied in the field of preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazole carboxamide and achieves the effect of high yield

Inactive Publication Date: 2007-07-11
BAYER IP GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this has the disadvantage that the 2-cyanoaniline required as starting material can only be obtained by a complex synthesis (cf. DE-A 2 115 624 and DE-A 2 115625)

Method used

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  • Method for producing 3,4-dichloro-n-(2-cyano-phenyl)-5-isothiazole carboxamide
  • Method for producing 3,4-dichloro-n-(2-cyano-phenyl)-5-isothiazole carboxamide
  • Method for producing 3,4-dichloro-n-(2-cyano-phenyl)-5-isothiazole carboxamide

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Experimental program
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Effect test

Embodiment 1

[0030]

[0031] At 60°C, 4.33 g (22 mmol) of 3,4- A solution of dichloroisothiazole carboxyl chloride. The reaction mixture was then stirred at 60° C. for a further 1 hour, after which it was concentrated under reduced pressure. The remaining residue was then stirred with 35 ml of water and filtered off with suction. The resulting still moist solid was boiled with isopropanol, cooled to room temperature, filtered off with suction and dried.

[0032] This gives 5.44 g of a white solid which, according to HPLC, consists of 100% N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazolecarboxamide. Therefore, the calculated yield was 86.0% of the theoretical yield.

[0033] 1 H-NMR (400MHz, d-DMSO): δ=7,27-7,31(m; 1H), 7,58-7,63(m; 1H), 7,88-7,94(m; 2H ), 8, 44-8, 50 (m; 2H), 12, 80 (s: 1H) ppm.

[0034] Melting point: 244-248°C.

Embodiment 2

[0036]

[0037] With stirring at 60°C, add 0.79g (2,5mmol) N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazolecarboxamide in 5ml dimethyl 0.416 g (3,5 mmol) of thionyl chloride was added dropwise to the suspension in methyl formamide. The reaction mixture was stirred at 60° C. for a further 4 hours, then it was cooled to room temperature, mixed with 5 ml of water and stirred for 15 minutes. The resulting solid was filtered off with suction, washed twice with 10 ml of water each time, and dried.

[0038] Thus obtained 0.63 g of white solid, according to 1 H-NMR spectrum, which consists of 91% of 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide. Therefore, the calculated yield was 76.9% of the theoretical yield.

[0039] 1 H-NMR (400MHz, d-DMSO): δ=7,47-7,51(m;1H),7,71-7,77(m;1H)7,79-7,81(m;1H) , 7, 92-7, 94 (m; 1H), 11, 05 (s; 1H) ppm.

Embodiment 3

[0041]

[0042]At 0°C, 3.16g (10mmol) N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazolecarboxamide was dissolved in 20ml dimethylformamide with stirring. 1.67g (14mmol) of thionyl chloride was added dropwise to the suspension. The reaction mixture was further stirred at 0°C for 2 hours, then 25 ml of water was added thereto under ice cooling, and the mixture was stirred for 15 minutes. The resulting solid was filtered off with suction, washed twice with 20 ml of water each time, and dried.

[0043] This gives 2.95 g of a white solid which, according to HPLC, consists of 99% of 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide. Therefore, the calculated yield was 98% of the theoretical yield.

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Abstract

The invention relates to a novel method for producing 3,4-dichloro-N-(2-cyano-phenyl)-5-isothiazole carboxamide. According to said method, a) 3,4-dichloro-isothiazole-5-carboxylic acid chloride is reacted with anthranilic acid amide in the presence of an acid acceptor and an aprotic diluent, and b) the N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazole carboxamide obtained is reacted with a dehydration agent optionally in the presence of an additional diluent. The N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-5-isothiazole carboxamide is novel.

Description

technical field [0001] The present invention relates to a novel process for the preparation of 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamides known to be useful as active compounds having microbicidal properties. Background technique [0002] It is known that when 3,4-dichloroisothiazole-5-carboxylic acid chloride is reacted with 2-cyano-aniline, 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazole can be obtained Carboxamides (see WO 99-24 413). The yield of the preparation method is high. However, this has the disadvantage that the 2-cyanoaniline required as starting material can only be obtained by a complex synthesis (cf. DE-A 2 115 624 and DE-A 2 115625). Therefore, it is necessary first to react anthranilamide with phosgene in the presence of dimethylformamide and then react the resulting N-2-cyanocyanide with sodium acetate in an aqueous medium in a second step. phenyl-N',N'-dimethylformamidinium hydrochloride for treatment. Contents of the invention [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D275/03C07D275/02A01N43/80
CPCC07D275/03
Inventor T·希姆莱
Owner BAYER IP GMBH
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