Reaction #1458425

Reaction equation

water

diphenylphosphine sulfide

N,N-diethylchloroacetamide

potassium hydroxide

→

N,N-Diethylcarbamoylmethyl-diphenylphosphine sulfide

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturewas cooled to 8–10° C. in an ice-water bath
2. 2
   Otherthe organic layer was separated
3. 3
   Washwashed with more water (25 ml)
4. 4
   Dryingdried over sodium sulfate
5. 5
   OtherThe solvent was removed under reduced pressure
6. 6
   Othera rotary evaporator
7. 7
   Otherthe oily residue was crystallized from ethyl acetate-hexane mixture
8. 8
   Otherto give 3.5 g (53%) of large cubes

Procedure

A stirred mixture of diphenylphosphine sulfide (4.365 g, 0.02 mol) and N,N-diethylchloroacetamide (4.189 g, 0.028 mol) in methylene chloride (80 ml) was cooled to 8–10° C. in an ice-water bath. Small pieces of solid potassium hydroxide (3.927 g, 0.07 mol) were added while stirring under nitrogen atmosphere. After 30 minutes, water (25 ml) was added and the organic layer was separated, washed with more water (25 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure using a rotary evaporator and the oily residue was crystallized from ethyl acetate-hexane mixture to give 3.5 g (53%) of large cubes. mp: 108–110° C.

Source