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

HRID 1957616Notes

Reaction equation

HRID 1957616 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-a8ca89cbd0c545b6ac325e177776e3bb
Source dataset
uspto-grants-1998_07
Patent number
US05786353

Reaction notes

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