Methyl Methanesulfonate → N-Methylcaprolactam

Temperature

25 °C

A suspension of 8.42 g of 57% NaH-mineral oil (4.8 g, 0.2 mole of NaH) was washed with 2 × 400 ml portions of dry toluene (distilled from CaH2). After the washing was completed, 350 ml of dry toluene was added and the suspension mechanically stirred while a solution of 20 g (0.177 mole) of azacycloheptan-2-one in 50 ml of dry toluene was added dropwise over 1 hour. After the addition was completed, the mixture was refluxed with stirring for 1 hour, then cooled to 25° C and 22.0 g (0.2 mole) of methyl mesylate was added dropwise over 1 hour. After the addition was complete, the mixture was warmed with stirring to 50° for 1 hour. The mixture was cooled, filtered and the solid was resuspended in 100 ml toluene and filtered. The combined filtrates were concentrated and the residue was distilled at 85°-87°/0.1mm to yield 20 g (88.85%) of product. On 5% SE-30 column it showed one peak.

1. washwas washed with 2 × 400 ml portions of dry toluene (distilled from CaH2)
2. addition350 ml of dry toluene was added
3. additionwas added dropwise over 1 hour
4. additionAfter the addition
5. temperaturethe mixture was refluxed
6. additionAfter the addition
7. temperaturethe mixture was warmed
8. stirringwith stirring to 50° for 1 hour
9. temperatureThe mixture was cooled
10. filtrationfiltered
11. filtrationfiltered
12. concentrationThe combined filtrates were concentrated
13. distillationthe residue was distilled at 85°-87°/0.1mm

ORD record

ord-0b0aa960bae64f25a2e2cabdb1736bbb

Source dataset

uspto-grants-1976_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03989816