2-Aminothiazole → HCID 3758127, compound

Participants

Reaction Steps

To a mixture of 2-aminothiazole (2.7 g, 0.0267 mol) and 2-bromo-3′-methoxyacetophenone (6.0 g, 0.0262 mol) is added absolute ethanol (100 ml). The reaction is allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture is reduced to half its original volume in vacuo. The remaining liquid is poured onto ice and the solution made basic by the addition of ammonium hydroxide solution (30%). The resulting fine solid is filtered and washed with water resulting in a dark yellow solid product. The solid product is dried in a vacuum oven at 50° C. to provide 6-(3-methoxyphenyl)-imidazo[2,1-b]thiazole (5.0 g, 81%). 400 MHz 1H NMR (DMSO-d6) δ 8.18 (s, 1H), 7.88 (d, J=4.4 Hz, 1H), 7.36-7.42 (m, 2H), 7.28 (t, J=8.1 Hz, 1H), 7.22 (d, J=4.4 Hz, 1H), 6.82 (ddd, J=8.1, 2.6, 1.1 Hz, 1H), 3.80 (s, 3H). LCMS: 231 [M+H].

Provenance & Evidence