Bromine → 2-Amino-6-benzylbenzothiazole

Reaction equation

[CH2:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([S-:17])#[N:16].[K+].BrBr>C(O)(=O)C>[NH2:16][C:15]1[S:17][C:13]2[CH:14]=[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=[CH:10][C:11]=2[N:12]=1

Participants

Procedure

A solution of 4-benzylaniline (0.916 g, 5.00 mmol) and KSCN (0.97 g, 10.0 mmol, 2.0 eq) in 10 mL acetic acid was cooled at about 5° C., and was treated dropwise with a solution of bromine (0.258 mL, 5.00 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 1 hour. The precipitate was filtered off and washed with Et2O. The obtained solid was neutralized with saturated sodium carbonate solution, and a new precipitate was formed. It was filtered off, washed with water and MeOH, and dried under vacuum to give the desired compound 1.06 g (88%). LC/MS 241.2 (M+1); LC retention time 2.46 min.