Triethylamine → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-N-methyl-2-methylbenzamide

HRID 962573Notes

Reaction equation

HRID 962573 reaction equation
[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:16][N:17]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25].C(N(CC)CC)C>O1CCCC1>[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][N:6]([C:31]([C:30]3[CH:29]=[CH:28][C:27]([N:17]([CH3:16])[C:18](=[O:26])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[CH:35][CH:34]=3)=[O:32])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 218370924-(N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride

Product 1

HCID 15307995N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-N-methyl-2-methylbenzamideYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.291 g of 6,11-dihydro-5H-dibenz[b,e]azepine, 0.518 g of 4-(N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride and 0.182 g of triethylamine in 10 ml of tetrahydrofuran is stirred at room temperature for 2 hours. The solvent is removed, the residue diluted with water and extracted with dichloromethane. The extract is washed with 1N HCl water, 1M NaHCO3, brine and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and chilled to give 0.52 g of crystals, m.p. 160°-170° C.

Workup

  1. customThe solvent is removed
  2. additionthe residue diluted with water
  3. extractionextracted with dichloromethane
  4. washThe extract is washed with 1N HCl water, 1M NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationThe filtrate is concentrated
  7. temperaturechilled

Sources & evidence

ORD record
ord-5aa386042ac04d6680fc4c19f5f7d73b
Source dataset
uspto-grants-1998_06
Patent number
US05760031

Reaction notes

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