Methyl iodide → N-Methylcaprolactam

Participants

Reaction Conditions

Reaction Steps

To a solution of ε-caprolactam (2.0 g, 17.6 mmol) in anhydrous THF (15 mL) at 0° C. was added NaH, 60% dispersion in oil (1.06 g, 26.0 mmol), and the mixture was stirred at 0° C. for 30 minutes. The cold bath was removed and the mixture was stirred at room temperature for 1 hour and then cooled again to 0° C. Methyl iodide (1.65 mL, 26.0 mmol) was added dropwise over 10 minutes, then the cold bath was removed and the mixture was stirred at room temperature for 18 hours. The excess NaH was quenched with methanol, THF was removed in vacuo and the crude was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate (2×30 mL), adding solid NaCl to break the emulsion. Organic washings were combined and dried over Na2SO4. Ethyl acetate was removed in vacuo and the crude product 206 (1.54 g, 68%) was used without further purification. MS (ESI)=128 (MH+).

Provenance & Evidence