Carbon Dioxide → 1-Benzoylazepan-2-one

HRID 377780Notes

Reaction equation

HRID 377780 reaction equation
CCN(C(C)C)C(C)C.[C:10]1(=[O:17])[NH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)=O>O.C1(C)C=CC=CC=1>[C:24]([N:16]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:17])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 7412Benzoyl chlorideHCID 7768CaprolactamHCID 10340Sodium CarbonateHCID 81531Diisopropylethylamine

Product 1

HCID 2244711-Benzoylazepan-2-oneYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

The comparison involves using soda instead of the Hunig base: 226.3 g of ε-caprolactam, 159.0 g of sodium carbonate and 1290 g of toluene are introduced into a 4 1 l flask. Under reflux, 281.1 g of benzoyl chloride are added dropwise over the course of 2 h at a rate such that CO2 evolution proceeds in a controlled manner. The mixture is then refluxed for a further 4 h. The reaction mixture is cooled to room temperature using water cooling (for about 15 min.), admixed with 500 g of water and vigorously stirred, and the aqueous phase is then separated off in a separating funnel. The toluene phase that remains is evaporated in a rotary evaporator at a temperature of 60° C. and residual toluene is removed in a vacuum drying oven, giving pale oil, which crystallizes upon cooling. M.p.: 69° C. The N-benzoylcaprolactam is obtained in a yield of 88% and a purity of 98%. The CO2 produced must be collected and disposed of separately.

Workup

  1. temperatureUnder reflux
  2. temperatureThe mixture is then refluxed for a further 4 h
  3. customthe aqueous phase is then separated off in a separating funnel
  4. customThe toluene phase that remains is evaporated in a rotary evaporator at a temperature of 60° C. and residual toluene
  5. customis removed in a vacuum
  6. customdrying oven
  7. customgiving pale oil, which
  8. customcrystallizes
  9. temperatureupon cooling

Sources & evidence

ORD record
ord-785af21c51d447288722aee681edefa7
Source dataset
uspto-grants-2000_02
Patent number
US06028192

Reaction notes

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