Water → N-[4-[(5,11-Dihydro-10H-dibenz[b,e][1,4]diazepin-10-yl)carbonyl]-3-chlorophenyl][1,1'-biphenyl]-2-carboxamide

HRID 1457700Notes

Reaction equation

HRID 1457700 reaction equation
[CH:1]1[C:11]2[CH2:10][NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:25]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:26]([C:31]([NH:33][C:34]2[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[C:36]([Cl:43])[CH:35]=2)=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=1.O>ClCCl>[CH:1]1[C:11]2[CH2:10][N:9]([C:38]([C:37]3[CH:41]=[CH:42][C:34]([NH:33][C:31]([C:26]4[C:25]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:32])=[CH:35][C:36]=3[Cl:43])=[O:39])[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 81531DiisopropylethylamineHCID 220996004-[([1,1'-Biphenyl]-2-carbonyl)amino]-2-chlorobenzoyl chloride

Product 1

HCID 22099587N-[4-[(5,11-Dihydro-10H-dibenz[b,e][1,4]diazepin-10-yl)carbonyl]-3-chlorophenyl][1,1'-biphenyl]-2-carboxamideYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.196 g of 5,11-dihydro-10H-dibenzo[b,e][1,4]diazepine, 0.155 g of N,N-diisopropylethylamine and 0.444 g of 4-[([1,1'-biphenyl]-2-carbonyl)amino]-2-chlorobenzoyl chloride in 12 ml of dichloromethane is stirred at room temperature overnight. The mixture is poured into water and extracted with dichloromethane. The extract is washed with 2N K2CO3, H2O, brine and dried (Na2 SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated to dryness and the residue triturated with ether and the solvent removed. The residue is triturated with dichloromethane to give 0.31 g of solid, m.p. 158° C.-184° C. Anal. Found for C33H24ClN3O2 1/2 H2O; C,73.7; H, 4.6; N,7.5; Cl,6.9.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with 2N K2CO3, H2O, brine
  3. customdried (Na2 SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationThe filtrate is concentrated to dryness
  6. customthe residue triturated with ether
  7. customthe solvent removed
  8. customThe residue is triturated with dichloromethane

Sources & evidence

ORD record
ord-5bbc1f50d4854d4591f113cea24b666b
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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