2-Methylpyridine → N-(2-Chloro-2-propen-1-yl)-N-(n-propyl)sulfamoyl chloride

HRID 1767263Notes

Reaction equation

HRID 1767263 reaction equation
[S:1](=[O:4])(=O)=[O:2].N1C=CC=CC=1C.[Cl:12][C:13](=[CH2:19])[CH2:14][NH:15][CH2:16][CH2:17][CH3:18].P(Cl)(Cl)([Cl:22])=O>ClCCCl.C(OC)(C)(C)C>[Cl:12][C:13](=[CH2:19])[CH2:14][N:15]([CH2:16][CH2:17][CH3:18])[S:1]([Cl:22])(=[O:4])=[O:2]

Participants

7

Reactant 4

HCID 79752-MethylpyridineHCID 24682Sulfur trioxideHCID 24813Phosphorus oxychlorideHCID 11344043HCID 11344043, compound

Product 1

HCID 11368249N-(2-Chloro-2-propen-1-yl)-N-(n-propyl)sulfamoyl chloride

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

35.7 g (0.256 mol) of sulfur trioxide as a 57.4% solution in 1,2-dichloroethane were added with stirring at from 0 to 5° C. within 15 min to a solution of 43.7 g (0.469 mol) of α-picoline in 200 ml of 1,2-dichloroethane, followed by washing with 40 ml of 1,2-dichloroethane and stirring for 15 min-until the temperature rose to 20° C. 28.5 g (0.192 mol) of 90% pure N-(2-chloro-2-propen-1-yl)-N-propylamine were then added within 15 min with stirring and external cooling at from 20 to 30° C., followed by washing with 40 ml of 1,2-dichloroethane and stirring at 50° C. for 15 min. After cooling to 23° C., 39.3 g (0.256 mol) of phosphorus oxychloride were added with stirring within 15 min, followed by washing with 120 ml of 1,2-dichloroethane and heating to 70° C. After stirring for 1 h, the reaction mixture was cooled and concentrated under reduced pressure, and the residue obtained was stirred with 100 ml of methyl tert-butyl ether each time. The methyl tert-butyl ether phases were decanted off and concentrated. The residue was distilled. 42.5 g (90.5% of theory) of the title compound having a boiling point of 67-71° C./0.4 mbar were obtained.

Workup

  1. washby washing with 40 ml of 1,2-dichloroethane
  2. customrose to 20° C
  3. stirringwith stirring
  4. washby washing with 40 ml of 1,2-dichloroethane
  5. stirringstirring at 50° C. for 15 min
  6. temperatureAfter cooling to 23° C.
  7. stirringwith stirring within 15 min
  8. washby washing with 120 ml of 1,2-dichloroethane
  9. temperatureheating to 70° C
  10. stirringAfter stirring for 1 h
  11. temperaturethe reaction mixture was cooled
  12. concentrationconcentrated under reduced pressure
  13. customthe residue obtained
  14. customThe methyl tert-butyl ether phases were decanted off
  15. concentrationconcentrated
  16. distillationThe residue was distilled
  17. customwere obtained

Sources & evidence

ORD record
ord-8f1d3b03651542c09c4c44c3966a8523
Source dataset
uspto-grants-2007_06
Patent number
US07232926B2

Reaction notes

Loading…