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

HRID 355834Notes

Reaction equation

HRID 355834 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.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1.ClCCl>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:6]2[CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 679746,11-Dihydro-5H-dibenz[b,e]azepineHCID 81531Diisopropylethylamine

Product 1

HCID 544990776,11Dihydro-5-(4-nitrobenzoyl)-5H-dibenz[b,e]azepineYield 96.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.34 g (12 mmol) of 6,11-dihydro-5H-dibenz[b,e]azepine, 2.23 g (12 mmol) of 4-nitrobenzoyl chloride, 1.94 g (15 mmol) of diisopropylethylamine and 70.5 mg of 4-(dimethylamino)pyridine in 25 ml of dichloromethane is stirred at room temperature for 2 hours, refluxed for 3 hours and allowed to stand at room temperature for 2 days. The mixture is washed with water, 1N sodium bicarbonate, water, 1N HCl, brine and dried (Na2SO4). The solvent is removed to give 4.0 g of solid. Trituration with ethyl acetate and filtering gives 2.85 g of off-white crystals, m.p. 185°-188° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. waitto stand at room temperature for 2 days
  3. washThe mixture is washed with water, 1N sodium bicarbonate, water, 1N HCl, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed

Sources & evidence

ORD record
ord-5abbe0daeaf34df097fe2f5d3746851e
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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