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

HRID 355908Notes

Reaction equation

HRID 355908 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-di-benz[b,e]azepine, 0.518 g of 4-[N-methyl-N-(2-methyl-benzoyl)amino]benzoyl chloride and 0.182 g of triethylamine in 10 ml of tetrahydrofuran is stirred at room temperature for 2 hours. The solyent is removed, the residue diluted with water and extracted with dichloromethane. The extract is washed with 1 N 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 solyent is removed
  2. additionthe residue diluted with water
  3. extractionextracted with dichloromethane
  4. washThe extract is washed with 1 N HCl water, 1M NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationThe filtrate is concentrated
  7. temperaturechilled

Sources & evidence

ORD record
ord-23ed4902dd57447db0cde6f8e545693b
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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