4-(Bromoacetyl)benzonitrile → 4-(2-Amino-1,3-thiazol-4-yl)benzonitrile

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=O)[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[NH2:13][C:14]([NH2:16])=[S:15].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:16][C:14]1[S:15][CH:8]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:13]=1

Participants

Procedure

Slurry 4-cyanophenacyl bromide (40 g, 179 mmol), thiourea (13.6 g, 181 mmol) and sodium bicarbonate (15.3 g, 181 mmol) in absolute ethanol (560 mL). Stir the mixture at reflux for 20 h under a nitrogen atmosphere. Cool the slurry to room temperature, filter, wash the solids with ethanol (100 mL), water (3×75 mL) and hexane (3×75 mL). Collect the yellow solid, add water (200 mL) and stir the slurry for 30 min at room temperate. Filter and wash the solid with hexane (excess). Slurry the solid in EtOAc (50 mL) and concentrate in vacuo twice to remove residual water. Collect the desired intermediate as a light yellow solid (36 g, 99%). MS (ES+) m/z: 202.1 (M+H)+.