2-Aminothiazole → HCID 11458707, compound

Participants

Reaction Steps

A solution of 2-chloro-5-nitropyridine (8.4 g, 53 mmol) and thiazol-2-amine (7.6 g, 76 mmol) in THF (250 mL) is cooled to 0° C. Sodium tert-butoxyde (30% w/w THF, 80 mL) is the added slowly over 15 minutes. The reaction mixture is then warmed slowly to room temperature and stirred 16 hours. The reaction mixture is then poured into a mixture of 1/1 ice/water (1.2 L) with stirring. The solid is filtered and air dried to give a powder (9.74 g, 83%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.17 (d, J=9.35 Hz, 2H), 7.20 (d, J=3.54 Hz, 1H), 7.49 (d, J=3.54 Hz, 1H), 8.43 (dd, J=9.35, 2.78 Hz, 1H), 9.15 (d, J=2.78 Hz, 1H), 12.17 (s, 1H). LCMS (M+H)+: 223.

Provenance & Evidence