Aniline → 2-(3-Chloro-phenoxy)-thiazole-4-carboxylic acid phenylamide

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Reaction Steps

1 g (3.75 mmol) 2-(3-chlorophenoxy)thiazole-4-carboxylic acid was added to 1 ml of SOCl2 and refluxed until the mixture gave a clear solution. Excess SOCl2 was evaporated in vacuo and the remaining acid chloride dissolved in 25 ml toluene. To this solution was added a solution of 0.34 g (3.65 mmol) aniline and 0.37 g triethylamine in 20 ml toluene. After stirring over night at room temperature the solution was washed with 20 ml dil. HCl, 20 ml water, 20 ml dil. NaOH and 20 ml water. The organic layer was dried with NaSO4 and evaporated to dryness to give 1.0 g (82.8%) 2-(3-chlorophenoxy)thiazole-4-carbanilide (m.p.:94°-95° C.).

Provenance & Evidence