Iodine → 4-(2-Amino-1,3-thiazol-4-yl)phenol

Participants

Reaction Steps

According to Group 4-scheme 2, 4'-hydroxyacetophenone (Aldrich Chemical Co., Milwaukee, Wis., USA) was reacted with thiourea and iodine according to the method of R. M. Dodson and L. C. King, J. Amer. Chem. Soc. 1945, 67, 2242 to give 4-(2-amino-4-thiazolyl)phenol (5). Reaction of the latter compound with 1,1-dimethylethyl 2-bromoacetate in the presence of potassium carbonate gave 1,1-dimethylethyl 2-{4-(2-amino-4-thiazolyl)phenoxy}acetate (6). Subsequent hydrolysis of the later compound gave the thiazolylphenoxyacetic acid derivative of formula 2 wherein R1C is amino.

Provenance & Evidence