Water → 4-[(2-Chloro-6,11-dihydro-5H-dibenz[b,e]azepin-5-yl) carbonyl]phenyl-2-methylbenzamide

HRID 1598728Notes

Reaction equation

HRID 1598728 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:15](=[O:23])[C:16]3[CH:21]=[CH:20][C:19](N)=[CH:18][CH:17]=3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1.C([N:28](CC)CC)C.[CH3:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37].O>ClCCl>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:42]4[C:34]([CH3:33])=[C:35]([CH:39]=[CH:40][CH:41]=4)[C:36]([NH2:28])=[O:37])=[CH:18][CH:17]=3)=[O:23])[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 544045372-Chloro-5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 867515734-[(2-Chloro-6,11-dihydro-5H-dibenz[b,e]azepin-5-yl) carbonyl]phenyl-2-methylbenzamideYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.349 g of 2-chloro-5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 0.131 g of triethylamine and 0.201 g of 2-methylbenzoyl chloride in 13 ml of dichloromethane is stirred at room temperature for 3 hours. The mixture is poured into water and the organic layer separated. The organic layer is washed with 1N HCl, H2O, 1N NaHCO3, brine and dried (Na2 SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated and the solid crystallized from dichloromethane-hexane to give 0.32 g of crystals, m.p. 187°-189° C.

Workup

  1. customthe organic layer separated
  2. washThe organic layer is washed with 1N HCl, H2O, 1N NaHCO3, brine
  3. customdried (Na2 SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with dichloromethane
  6. concentrationThe filtrate is concentrated
  7. customthe solid crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-066e90ca54d64bc68552bc15af9a66fa
Source dataset
uspto-grants-1998_04
Patent number
US05739128

Reaction notes

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