Water → Acetamide, 2-(diphenylphosphinothioyl)-N,N-diethyl-

HRID 1371243Notes

Reaction equation

HRID 1371243 reaction equation
[C:1]1([PH:7](=[S:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([N:17]([CH2:22][CH3:23])[C:18](=[O:21])[CH2:19]Cl)[CH3:16].[OH-].[K+].O>C(Cl)Cl>[CH2:15]([N:17]([CH2:22][CH3:23])[C:18]([CH2:19][P:7](=[S:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:21])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 16844Chloro-N,N-diethylacetamideHCID 178528040HCID 178528040, compound

Product 1

HCID 796778Acetamide, 2-(diphenylphosphinothioyl)-N,N-diethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. temperaturewas cooled to 8–10° C. in an ice-water bath
  2. customthe organic layer was separated
  3. washwashed with more water (25 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customa rotary evaporator
  7. customthe oily residue was crystallized from ethyl acetate-hexane mixture
  8. customto give 3.5 g (53%) of large cubes

Sources & evidence

ORD record
ord-415fe52e9f254e298e86d93ccb87466a
Source dataset
uspto-grants-2007_01
Patent number
US07157219B2

Reaction notes

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