Terephthaloyl chloride → 2H-Azepin-2-one, 1,1'-(1,4-phenylenedicarbonyl)bis[hexahydro-

HRID 265721Notes

Reaction equation

HRID 265721 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:13]1(=[O:20])[NH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C1CCCCC1.N1C=CC=CC=1>[C:1]([N:19]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:20])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:19]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]2=[O:20])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7488Terephthaloyl chlorideHCID 7768Caprolactam

Product 1

HCID 758792H-Azepin-2-one, 1,1'-(1,4-phenylenedicarbonyl)bis[hexahydro-

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8078CyclohexaneSolvent

Procedure

Terephthaloyl chloride (51 g, 0.25 mol) is added in the course of 30 minutes to a solution of ε-caprolactam (56.6 g, 0.5 mol) in 400 ml of cyclohexane and 117 ml of pyridine at room temperature. The mixture is then refluxed for 4 h. After cooling, the resulting light yellow precipitate is filtered off by suction, washed with water and dried. Yield 81 g (91%).

Workup

  1. temperatureThe mixture is then refluxed for 4 h
  2. temperatureAfter cooling
  3. filtrationthe resulting light yellow precipitate is filtered off by suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f7051754a9834235a3ddac34e2b347c0
Source dataset
uspto-grants-1997_07
Patent number
US05648521

Reaction notes

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