2-Aminothiazole → HCID 54704472, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-hydroxy-6H-thieno[2,3-b]thiopyran-5-carboxylate 7,7-dioxide (5.2 g, 0.02 mole), 2-aminothiazole (3.0 g, 0.03 mole) and xylene (175 ml) is warmed and filtered from the polymeric products. The filtrate is refluxed for 30 min. when some more polymeric product is formed. It is filtered again, and the filtrate refluxed for 1.5 hrs. The mixture is cooled to 5° C. in an ice-bath, and the resulting crystalline product is collected. It is dissolved in THF, treated with charcoal and filtered. The filtrate is concentrated to give the desired product (1.4 g, 21%), m.p. 215°-216° C. IR (Nujol) 3100 (broad, NH and OH); 1590 (CONH); 1155 (SO2) cm-1. NMR (DMSO) δ 11.0 (b, ~2, NH and OH); 8.1 (d, 1, C3 '); 7.5 (m, 2, C2 -C3); 7.15 (d, 1, C4 '); 4.6 (s, 2, CH2). λmaxEtOH 360 (14,600), 267 (12,400), 246 (11,600) mμ; mol. ion. 328.

Provenance & Evidence