Triethylamine → N-[4-(6,11-Dihydro-dibenzo[b,e]azepine-5-carbonyl)-phenyl]-2-methyl-benzamide

HRID 1288955Notes

Reaction equation

HRID 1288955 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:5].[CH:20]1[C:30]2[CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[CH2:26][NH:25][C:24]=2[CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>O1CCCC1>[CH:20]1[C:30]2[CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=3[CH2:26][N:25]([C:11]([C:10]3[CH:14]=[CH:15][C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=4[CH3:1])=[CH:8][CH:9]=3)=[O:12])[C:24]=2[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Product 1

HCID 15307968N-[4-(6,11-Dihydro-dibenzo[b,e]azepine-5-carbonyl)-phenyl]-2-methyl-benzamideYield 108.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.27 g (1 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 2 ml of tetrahydrofuran is added 0.20 g (1 mmol) of 6,11-dihydro-5H-dibenz[b,e]azepine and 0.20 g of triethylamine. The mixture is stirred at room temperature for 3 hours and the solvent removed under vacuum. To the residue is added 1N HCl and the mixture extracted with ethyl acetate (20 ml) and the extract washed with saturated NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate evaporated. The residue is triturated with ether-hexane and filtered to give 0.47 g of a white solid: Mass Spectrum; EI 433 (M+1); EI-high resolution 432.1842.

Workup

  1. customthe solvent removed under vacuum
  2. additionTo the residue is added 1N HCl
  3. extractionthe mixture extracted with ethyl acetate (20 ml)
  4. washthe extract washed with saturated NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  7. customthe filtrate evaporated
  8. customThe residue is triturated with ether-hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-1ce24fb65ec9421b9fa939195fe16961
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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