N-[(2-fluoro-5-nitrophenyl)carbamothioyl]benzamide → 5-Nitro-1,3-benzothiazol-2-amine

HRID 723950Notes

Reaction equation

HRID 723950 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

HCID 817311N-[(2-fluoro-5-nitrophenyl)carbamothioyl]benzamideHCID 10942334Sodium Methoxide

Product 1

HCID 27547595-Nitro-1,3-benzothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. stirringthe mixture stirred at room temperature for 17 hours
  2. temperatureAfter this time, the reaction mixture was cooled in an ice bath
  3. filtrationfiltered
  4. washThe precipitate was washed with water (7.10 g, 86%)

Sources & evidence

ORD record
ord-2bb3380b827d4311a12cc1309e178602
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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