Triethylamine → 1H-1-Benzazepine, 2,3,4,5-tetrahydro-1-(4-nitrobenzoyl)-

HRID 362349Notes

Reaction equation

HRID 362349 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>ClCCl>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([N:1]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:27])=[CH:29][CH:30]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 106376761H-1-Benzazepine, 2,3,4,5-tetrahydro-1-(4-nitrobenzoyl)-Yield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5.0 g of 1,2,3,4-tetrahydro-5H-1-benzazepine and 5.91 ml of triethylamine in 50 ml of dichloromethane, chilled in an ice bath, is added, dropwise, 6.32 g of 4-nitrobenzoyl chloride in 75 ml of dichloromethane. The mixture is stirred at 0° C. for 1.5 hr and then at room temperature for 18 hours. The mixture is washed with H2O, 2M HCl, 1M NaOH and dried (Na2SO4). The solvent is removed and the residue re-crystallized from ethanol with the aid of activated carbon to give 7.75 g of light yellow crystals, m.p. 148.5°-150.5° C.

Workup

  1. additionis added
  2. waitat room temperature for 18 hours
  3. washThe mixture is washed with H2O, 2M HCl, 1M NaOH
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed
  6. customthe residue re-crystallized from ethanol with the aid of activated carbon

Sources & evidence

ORD record
ord-c8277afe476448778eb1c90f8240dbc4
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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