Thioacetamide → Ethyl 2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 1418115Notes

Reaction equation

HRID 1418115 reaction equation
OC1O[C@@H](CO)[C@H](O)[C@H](O)[C@H]1O.[F:13][C:14]([F:25])([F:24])[C:15](=O)[CH:16](Cl)[C:17]([O:19][CH2:20][CH3:21])=[O:18].[C:26]([NH2:29])(=[S:28])[CH3:27]>>[CH3:27][C:26]1[S:28][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([C:14]([F:25])([F:24])[F:13])[N:29]=1

Participants

4

Reactant 3

HCID 2723949ThioacetamideHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoateHCID 10219674L-Altrose

Product 1

HCID 1486077Ethyl 2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Procedure

U.S. Pat. No. 5,045,554 (Alt et al., 9/91), herein incorporated by reference, discloses the reaction of ethyl 4,4,4-trifluoro-2-chloroacetoacetate and thioacetamide to produce ethyl 2-methyl-4-(trifluoromethyl)thiazole-5-carboxylate, which was in turn used to produce fungicidal thiazolecarboxanilides. The reaction produced the thiazole in one step by refluxing the reactants in dimethylformamide, but had only a 38% isolated yield.

Sources & evidence

ORD record
ord-ecb65e45935042f6b4a113ea797ad146
Source dataset
uspto-grants-1999_03
Patent number
US05880288

Reaction notes

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