Methyl Methanesulfonate → N-Methylcaprolactam

HRID 2309071Notes

Reaction equation

HRID 2309071 reaction equation
C[O-].[Na+].C[Si](C)(C)[N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:13].[CH3:16]S(OC)(=O)=O>COCCOC>[CH3:16][N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:13]

Participants

5

Reactant 3

HCID 4156Methyl MethanesulfonateHCID 10942334Sodium MethoxideHCID 114239991-Trimethylsilanyl-azepan-2-one

Product 1

HCID 17369N-Methylcaprolactam

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5.4 g (0.1 mol) of sodium methylate and 18.5 g (0.1 mol) of N-trimethylsilylcaprolactam are introduced successively into 150 ml of 1,2-dimethoxyethane, and the mixture is stirred at room temperature for 30 minutes. Then 11 g (0.1 mol) of methyl methanesulfonate are added dropwise. After the reaction mixture has been stirred at 50° C. for a further one hour, it is cooled, the sodium mesylate is removed by filtration with suction, and the filtrate is evaporated. The oily residue is distilled in vacuo.

Workup

  1. stirringAfter the reaction mixture has been stirred at 50° C. for a further one hour
  2. temperatureit is cooled
  3. customthe sodium mesylate is removed by filtration with suction
  4. customthe filtrate is evaporated
  5. distillationThe oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-6e6fc79716314fec81b7435f06423741
Source dataset
uspto-grants-1987_09
Patent number
US04692523

Reaction notes

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