Caprolactam → Bis(2-oxoazepan-1-yl)ethane-1,2-dione

HRID 265724Notes

Reaction equation

HRID 265724 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]1(=[O:14])[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1(C)C=CC=CC=1>[C:1]([N:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:14])(=[O:5])[C:2]([N:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:14])=[O:3]

Participants

4

Reactant 2

HCID 7768CaprolactamHCID 65578Oxalyl chloride

Product 1

HCID 19035121Bis(2-oxoazepan-1-yl)ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Oxalyl dichloride (63.4 g, 0.5 mol) is added dropwise in the course of 30 minutes to a solution of ε-caprolactam (107.6 g, 0.95 mol) in toluene (300 ml). The internal temperature increases in the course of this from 20 to 60° C. The mixture is then refluxed for 2 hours. After removal of the solvent in vacuo, the resulting oil is taken up in methanol, the colorless precipitate precipitating out in the cold is isolated and dried. Yield 113.8 g (86%).

Workup

  1. temperatureThe mixture is then refluxed for 2 hours
  2. customAfter removal of the solvent in vacuo
  3. customthe colorless precipitate precipitating out in the
  4. customcold is isolated
  5. customdried

Sources & evidence

ORD record
ord-7da9a30f00b047569737a82a5796d70a
Source dataset
uspto-grants-1997_07
Patent number
US05648521

Reaction notes

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