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

HRID 1808499Notes

Reaction equation

HRID 1808499 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-6909b5ef4068425a8c915230ad0e4ad6
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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