Benzoyl chloride, 3-nitro- → 4,5-Dimethoxy-2-(3-nitrophenyl)aminobenzamide

HRID 1406987Notes

Reaction equation

HRID 1406987 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)C(Cl)=O)([O-:17])=[O:16]>N1C=CC=CC=1>[CH3:12][O:11][C:9]1[C:8]([O:13][CH3:14])=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([NH:1][C:25]2[CH:24]=[CH:20][CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:26]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 108672362-Amino-4,5-dimethoxybenzamide

Product 1

HCID 668250984,5-Dimethoxy-2-(3-nitrophenyl)aminobenzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 2-amino-4,5-dimethoxybenzamide (5.05 g, 25.7 mmole) and 3-nitro benzoyl chloride (5.2 g, 28.0 mmole) CHCl3 (120 ml) was added pyridine (50 ml) drop wise at RT. The reaction mixture was stirred at RT for 24 h. The solvent was removed in vacuo and residue was triturated with Et2O, filtered and dried under high vacuum to give 4,5-dimethoxy-2-(3-nitrophenyl)aminobenzamide, which was used directly in the next step.

Workup

  1. customThe solvent was removed in vacuo and residue
  2. customwas triturated with Et2O
  3. filtrationfiltered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-83c2cb64d58d4468983cad8a900652a1
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

Loading…