Benzoyl isothiocyanate → 3-(Benzoylcarbamothioylamino)-5-methoxy-benzoic acid
Reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:16]([OH:18])=[O:17]>CC(C)=O>[C:1]([NH:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:16]([OH:18])=[O:17])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Benzoyl isothiocyanate (169 μl, 1.25 mmol) was added to a solution of 3-amino-5-methoxy-benzoic acid (0.2 g, 1.19 mmol) in acetone (10 mL). The reaction was stirred at ambient temperature and a thick precipitate formed after 10 minutes. LCMS indicated complete conversion of the starting material. The solvent was removed in vacuo and the crude material triturated with iso-hexane, dried under reduced pressure and used directly in the next step.