2-Aminothiazole → 6-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O.[OH-].[NH4+]>C(O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:1]=[C:2]3[N:6]([CH:8]=2)[CH:5]=[CH:4][S:3]3)=[CH:12][CH:13]=1

Participants

Procedure

To a mixture of 2-aminothiazole (H) (23.7 g, 0.23 mol) and 2-bromo-1-(4-fluorophenyl)-ethanone (I) (50 g, 0.23 mol) is added absolute ethanol (600 mL). The reaction is allowed to reflux with vigorous stirring for 16 hours. 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. The dark yellow solid so obtained is dried in a vacuum oven at 50° C. to provide 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (43.0 g, 86%).