Bromine → 7-(Hydroxymethyl)-N-mesityl-1,3-benzothiazol-2-amine
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])=[S:11])[CH:6]=[CH:7][CH:8]=1.BrBr>C(O)(=O)C>[OH:1][CH2:2][C:3]1[C:4]2[S:11][C:10]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:9][C:5]=2[CH:6]=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 0.25 g (0.83 mmol) of 1-(3-hydroxymethylphenyl)-3-mesitylthiourea in 5 mL of glacial acetic acid was added 47 μL (0.91 mmol) of bromine. The reaction was stirred for 5 min and concentrated in vacuo to give the title compound and its regioisomer as their O-acetates. The mixture was stirred in methanol over potassium carbonate for 1 h. The mixture was concentrated in vacuo, slurried in dichloromethane and filtered. The filtrate was concentrated and purified by flash chromatography eluting with a 33-66% ethyl acetate/hexanes gradient mixture to give 0.070 g (28%) of the title compound as a white solid.