2-Methylpyridine → N-Methyl-N-(1-methylethyl)sulfamoyl chloride

Temperature

20 °C

63.2 g (0.41 mol) of sulfur trioxide as a 52% solution in 1,2-dichloroethane were added with stirring at from 0 to 5° C. within 15 min to a solution of 70.0 g (0.752 mol) of α-picoline in 250 ml of 1,2-dichloroethane, followed by washing with 50 ml of 1,2-dichloroethane and stirring for 15 min until the temperature rose to 25° C. 26.3 g (0.342 mol) of 95% pure N-methyl-N-[1-methylethyl]amine were then added within 15 min with stirring at from 20 to 35° C., followed by washing with 50 ml of 1,2-dichloroethane and stirring at 55° C. for 15 min. After cooling to 20° C., 42.7 g (0.205 mol) of phosphorus pentachloride were added with stirring at from 20 to 32° C. within 15 min with external cooling, followed by washing with 150 ml of 1,2-dichloroethane. After stirring at 70° C. for 2 h, the reaction mixture was concentrated under reduced pressure and distilled via a Normag column head having a 10 cm column. 35 g (59.6% of theory) of the title compound having a boiling point of 110-115° C./30 mbar were obtained. Refractive index nD23=1.4620.

1. washby washing with 50 ml of 1,2-dichloroethane
2. customrose to 25° C
3. stirringwith stirring at from 20 to 35° C.
4. washby washing with 50 ml of 1,2-dichloroethane
5. stirringstirring at 55° C. for 15 min
6. stirringwith stirring at from 20 to 32° C. within 15 min with external cooling
7. washby washing with 150 ml of 1,2-dichloroethane
8. stirringAfter stirring at 70° C. for 2 h
9. concentrationthe reaction mixture was concentrated under reduced pressure
10. distillationdistilled via a Normag column head
11. customwere obtained

ORD record

ord-cbfd198bdc1f4e019a64013a1957bcff

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07232926B2