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

HRID 1721663Notes

Reaction equation

HRID 1721663 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 recrystallized 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 recrystallized from ethanol with the aid of activated carbon

Sources & evidence

ORD record
ord-12c3b6a3c2a444ee9aebd48921aac782
Source dataset
uspto-grants-1996_04
Patent number
US05512563

Reaction notes

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