Methyl iodide → N-Methylcaprolactam

Temperature

0 °C

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+).

1. customThe cold bath was removed
2. stirringthe mixture was stirred at room temperature for 1 hour
3. temperaturecooled again to 0° C
4. customthe cold bath was removed
5. stirringthe mixture was stirred at room temperature for 18 hours
6. customThe excess NaH was quenched with methanol, THF
7. customwas removed in vacuo
8. customthe crude was partitioned between ethyl acetate and water
9. washThe aqueous phase was washed with ethyl acetate (2×30 mL)
10. additionadding solid NaCl
11. dry with materialdried over Na2SO4
12. customEthyl acetate was removed in vacuo
13. customthe crude product 206 (1.54 g, 68%) was used without further purification

ORD record

ord-29fcfe8d3a25434bb33211bcdcf52ea6

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07288567B2