Triethylamine → N-(3-dimethylaminophenyl)-3-(3-methoxybenzamido)-4-methylbenzamide

HRID 502027Notes

Reaction equation

HRID 502027 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]([CH3:23])[CH3:22])[CH:16]=1)=[O:13].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34]>C(Cl)Cl>[CH3:22][N:21]([CH3:23])[C:17]1[CH:16]=[C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:24]=[CH:25][C:26]([CH3:27])=[C:9]([NH:8][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][CH:38]=[C:30]([O:29][CH3:28])[CH:31]=3)[CH:10]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 226361113-amino-N-(3-dimethylaminophenyl)-4-methylbenzamide

Product 1

HCID 22636140N-(3-dimethylaminophenyl)-3-(3-methoxybenzamido)-4-methylbenzamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.101 g) was added to a stirred mixture of 3-amino-N-(3-dimethylaminophenyl)-4-methylbenzamide (0.135 g), 3-methoxybenzoyl chloride (0.13 g) and methylene chloride (5 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was evaporated and the residue was triturated under a mixture of ethyl acetate and isohexane. There was thus obtained the title compound as a solid (0.156 g); Mass Spectrum: M+H+ 404.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate
  3. customThe organic phase was evaporated
  4. customthe residue was triturated under a mixture of ethyl acetate and isohexane

Sources & evidence

ORD record
ord-3aceccd5cc574c3383d9f0c6aca5373a
Source dataset
uspto-grants-2010_08
Patent number
US07772432B2

Reaction notes

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