O-Toluidine → 4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]-N-(2-methylphenyl)benzamide

HRID 962565Notes

Reaction equation

HRID 962565 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][N:6]([C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=3)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:34][C:35]1[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=1[NH2:37]>ClCCl>[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:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:37][C:36]4[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=4[CH3:34])=[O:23])=[CH:20][CH:19]=3)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 538022444-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoyl chloride

Product 1

HCID 153079914-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]-N-(2-methylphenyl)benzamideYield 5.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 0.362 g of 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoyl chloride and 0.101 g of triethylamine in 5 ml of dichloromethane is added a solution of 0.129 g of 2-methylaniline in 3 ml of dichloromethane. The mixture is stirred 1.5 hr at room temperature and then washed with H2O 1N HCl, 1M NaHCO3, brine and dried (Na2SO4). The solvent is removed to give a solid. The solid is dissolved in dichloromethane and filtered through a thin pad of hydrous magnesium silicate with dichloromethane as eluent to give 0.025 g of crystals, m.p. 214°-216° C.

Workup

  1. washwashed with H2O 1N HCl, 1M NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed
  4. customto give a solid
  5. filtrationfiltered through a thin pad of hydrous magnesium silicate with dichloromethane as eluent

Sources & evidence

ORD record
ord-9bed34be56464b02a0477c9340822220
Source dataset
uspto-grants-1998_06
Patent number
US05760031

Reaction notes

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