4-Nitrobenzoyl chloride → 2-Chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 362347Notes

Reaction equation

HRID 362347 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1.[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18].C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([C:24](=[O:25])[C:23]3[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:28][CH:27]=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

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 537916382-chloro-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 539356852-Chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineYield 68.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.05 g of 2-chloro-6,11-dihydro-5H-dibenz[b,e]azepine, 2.15 g of 4-nitrobenzoyl chloride, 1.50 g of N,N-diisopropylethylamine, 54 mg of 4-(dimethylamino)pyridine in 15 ml of dichloromethane is refluxed for 18 hours. The mixture is cooled and washed with H2O, 1N HCl, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated and the residue recrystallized from dichloromethane-hexane to give 2.33 g of crystals, m.p. 198°-201° C.

Workup

  1. temperatureis refluxed for 18 hours
  2. temperatureThe mixture is cooled
  3. washwashed with H2O, 1N HCl, 1M NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  6. washthe pad washed with dichloromethane
  7. concentrationThe filtrate is concentrated
  8. customthe residue recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-a69f4319ae88435aa224946774acfc55
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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