4-(4-Methylphenyl)-1,3-thiazole-2-carboxylic acid → HCID 178423924, compound

Participants

Reaction Steps

A mixture of 4-(4-methylphenyl)-2-thiazolecarboxylic acid (300 mg, 1.37 mmol) and N,N -carbonyl diimidazole (CDI) (444.3 mg, 2.74 mmol) dissolved in dry DMF (5 ml) was stirred at room temperature for 1 hour. Under the same conditions, a solution of 5-aminotetrazole (139.5 mg, 1.64 mmol) in dry DMF was added thereto, and the resulting mixture was allowed to react at 85° C. for 2 hours. After removing of the solvent from the reaction mixture by distillation, the residue was treated with water and acidified with 1N-HCl to pH 2. The deposited solids were filtered with suction, washed with water and recrystallized from methanol-THF-water to give 258 mg (yield 66%) of 4-(4-methylphenyl)-N-(1H-tetrazole-5-yl)-2-thiazolecarboxamide as pale yellow crystals, m.p. 276°-278° C.

Provenance & Evidence