N-[(2-fluoro-5-nitrophenyl)carbamothioyl]benzamide → 5-Nitro-1,3-benzothiazol-2-amine
Reaction equation
C[O-].[Na+].C([NH:12][C:13]([NH:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1F)=[S:14])(=O)C1C=CC=CC=1>CO>[N+:22]([C:20]1[CH:19]=[CH:18][C:17]2[S:14][C:13]([NH2:12])=[N:15][C:16]=2[CH:21]=1)([O-:24])=[O:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methanol (1.6 L) was added sodium methoxide (8.64 g). While stirring, 1-benzoyl-3-(2-fluoro-5-nitro-phenyl)-thiourea (16 g) was added as a solid and the mixture stirred at room temperature for 17 hours. After this time, the reaction mixture was cooled in an ice bath and then filtered. The precipitate was washed with water (7.10 g, 86%). 1H-NMR δ: 8.05 (d, 1H, J=2.2 Hz), 7.97 (brs, 2H), 7.93 (s, 1H), 7.90 (d, 1H, J=2.2 Hz); MS (ESI) 195.8 (M+1, 100%).