Water → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-phenyl][1,1'-biphenyl]-2-carboxamide

HRID 1457701Notes

Reaction equation

HRID 1457701 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.[C:16]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:17]([C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)C(C)C)(C)C.O>ClCCl.CCCCCC.C(OCC)(=O)C>[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:29]([C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:22]([C:17]4[C:16]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:23])=[CH:33][CH:32]=3)=[O:30])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 81531DiisopropylethylamineHCID 114505014-(2-Phenylbenzoylamino)-benzoylchloride

Product 1

HCID 22099947N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-phenyl][1,1'-biphenyl]-2-carboxamideYield 33.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 6,11-dihydro-5H-dibenz[b,e]azepine (0.195 g), 4-[([1,1'-biphenyl]-2-carbonyl)amino]benzoyl chloride (0.41 g) and 0.155 g of N,N-diisopropylethylamine in 12 ml of dichloromethane is stirred at room temperature for 3 hours. The mixture is poured into water and extracted with dichloromethane. The extract is washed with H2O, saturated NaHCO3, H2O, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filter pad washed with dichloromethane. The filtrate is concentrated to dryness to give 0.66 g of a yellow l , solid. Chromatography on thick layer silica gel plates with hexane-ethyl acetate (1.5:1) gives crystals (0.165 g) (from dichloromethane-ethyl acetate), m.p. 224° C.-225° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with H2O, saturated NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe filter pad washed with dichloromethane
  6. concentrationThe filtrate is concentrated to dryness
  7. customto give 0.66 g of a yellow l , solid

Sources & evidence

ORD record
ord-28c6b7f885f443c58fb52e2651d50465
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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