Pyridine → beta,beta,beta-Trichloroethoxycarbonylsulfenyl Chloride

To an ice cold vigorously stirred (mechanical stirrer) solution of trichloroethanol (50.0 ml, 0.52 mol) and pyridine (42.0 ml, 0.52 mol) in 300 ml of methlene chloride, chlorocarbonylsulfenyl chloride (43.5 ml, 0.52 mol) was added dropwise over 30 min. After the addition the solution was stirred at 0° for 1.5 hr. The ice bath was removed and the stirring continued for 1.5 hr. The mixture (solid formed) was washed with ice--H2O and ice cold sat. NaCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure. After removal of the solvent an oily solid remained. The solid was removed by triterration with ether and filtration of the solid. The filtrate was condensed under reduced pressure and the process repeated until, after removal of the solvent from the filtrate, the liquid could be filtered without the aid of solvent. The yellow liquid was distilled under reduced pressure: bp 54°-59° (0.25 mm; bath temp. 80°-90°); NMR (CDCl3 ) δ 5.0 (S, 2H).

1. additionwas added dropwise over 30 min
2. additionAfter the addition the solution
3. customThe ice bath was removed
4. waitthe stirring continued for 1.5 hr
5. customThe mixture (solid formed)
6. washwas washed with ice
7. dry with materialThe organic layer was dried (MgSO4)
8. customthe solvent removed under reduced pressure
9. customAfter removal of the solvent an oily solid
10. customThe solid was removed by triterration with ether and filtration of the solid
11. customcondensed under reduced pressure
12. customafter removal of the solvent from the filtrate
13. filtrationthe liquid could be filtered without the aid of solvent
14. distillationThe yellow liquid was distilled under reduced pressure
15. custombp 54°-59° (0.25 mm; bath temp. 80°-90°)

ORD record

ord-f324340781e54155a521a8998772c869

Source dataset

uspto-grants-1981_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04265882