Triethylamine → N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-chloromethylbenzamide

HRID 967905Notes

Reaction equation

HRID 967905 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:19]=2)[CH:12]=[CH:13][C:14]=1[CH3:15].[Cl:28][CH2:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34]>C(Cl)Cl>[CH3:25][N:24]([CH3:26])[C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([NH:16][C:11]1[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([NH:8][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][CH:38]=[C:30]([CH2:29][Cl:28])[CH:31]=2)[CH:10]=1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 22057981HCID 22057981, compound

Product 1

HCID 22291114N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-chloromethylbenzamideYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.55 ml) was added to a stirred mixture of N-(3-amino-4-methylphenyl)-3-dimethylaminobenzamide (3.0 g), 3-chloromethylbenzoyl chloride (2.76 g) and methylene chloride (50 ml) and the reaction mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under water. The solid so obtained was isolated, washed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane and dried under vacuum at 55° C. There was thus obtained the title compound (4.8 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.96 (s, 6H), 4.84 (s, 2H), 6.9 (d, 1H), 7.26 (m, 3H), 7.5-7.7 (m, 3H), 7.8-8.1 (m, 4H), 9.97 (s, 1H), 10.09 (s, 1H); Mass Spectrum: M−H− 420.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under water
  3. customThe solid so obtained
  4. customwas isolated
  5. washwashed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane
  6. customdried under vacuum at 55° C

Sources & evidence

ORD record
ord-7bc1ed61f08248018780c1649ceb2378
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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