Ammonia → 5-Amino-3-methyl-1,2-thiazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a chilled solution of sulfuric acid (7.2 volumes, 12.9 equivs) was charged 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (1.0 equiv). The temperature was maintained below 55° C. The reaction mixture was heated to 70° C. and held for 1 hour until TLC showed disappearance of starting material. The mixture was cooled to 60-65° C. before the ammonia (21 volumes) was charged to pH 10. The mixture was cooled to 20° C., aged overnight and filtered. The resulting solid was washed with dilute ammonia (3.6 volumes) and dried at 40° C. to give a pale brown solid (typical yield 80%).1H NMR (300 MHz, DMSO-d6) δ 2.46(s, 3H), 6.28 (s, 1H).

Provenance & Evidence