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

HRID 1938229Notes

Reaction equation

HRID 1938229 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 H2 O, 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 H2 O, 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-cb75564683ad4df1871c7a54585e4ee8
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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