Tert-Butylamine → N-tert-butylmethanesulfonamide

Temperature

0 °C

To a 0° C. solution of 10 g (136.7 mmol) of t-butylamine and 15.2 g (150.4 mmol) of triethylamine in 350 mL of dichloromethane was added 15.7 g (136.7 mmol) of methanesulfonyl chloride in 20 mL of dichloromethane over 15 minutes. Continue stirring at 0° C. for 30 minutes then warm to room temperature over one hour. The mixture was washed once with 250 mL of 10% aqueous sodium bisulfate. The organic portion was separated and the aqueous portion was extracted two times with 100 mL each of dichloromethane. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The residue was recrystallized from petroleum ether and dried in vacuo to afford 12.2g (59%) N-t-butyl methanesulfonamide.

1. temperaturethen warm to room temperature over one hour
2. washThe mixture was washed once with 250 mL of 10% aqueous sodium bisulfate
3. customThe organic portion was separated
4. extractionthe aqueous portion was extracted two times with 100 mL each of dichloromethane
5. dry with materialThe combined organics were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was recrystallized from petroleum ether
9. customdried in vacuo

ORD record

ord-8ff8882027f24bf2b97ca4872494ddcd

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552086B1