O,O-Diethyl dithiophosphate → HCID 53825183, compound

HRID 746279Notes

Reaction equation

HRID 746279 reaction equation
[CH3:1][CH2:2][O:3][P:4]([SH:9])([O:6][CH2:7][CH3:8])=[S:5].[Br:10][C:11]1[CH:12]=[C:13]([C:17](=[O:23])[CH:18]=[CH:19][C:20]([OH:22])=[O:21])[CH:14]=[CH:15][CH:16]=1>CC(C)=O>[Br:10][C:11]1[CH:12]=[C:13]([C:17](=[O:23])[CH:18]=[C:19]([S:5][P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:2][CH3:1])=[S:9])[C:20]([OH:22])=[O:21])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 9274O,O-Diethyl dithiophosphateHCID 533962204-(3-Bromophenyl)-4-oxobut-2-enoic acid

Product 1

HCID 53825183HCID 53825183, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.12 g (0.006 mole) of O,O-diethyldithiophosphoric acid were added dropwise to a solution of 1.28 g (0.005 mole) of 4-(3-bromophenyl)-4-oxo-2-butenoic acid in 20 ml of acetone, and then the mixture was stirred overnight at room temperature. At the end of this time, the solvent was distilled off and the residue was extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulphate, after which the solvent was distilled off. The residue was subjected to column chromatography through silica gel, eluted with a 4:1 by volume mixture of benzene and ethyl acetate. The resulting solid was recrystallised from a mixture of benzene and hexane, to give 1.54 g (yield 69.8%) of the desired 4-(3-bromophenyl)-2-diethoxyphosphinothioylthio-4-oxobutenoic acid, melting at 107°-111° C.

Workup

  1. distillationAt the end of this time, the solvent was distilled off
  2. extractionthe residue was extracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. distillationafter which the solvent was distilled off
  6. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate
  7. customThe resulting solid was recrystallised from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-6b191f1da78045a0b4731a4f9758c81d
Source dataset
uspto-grants-1986_07
Patent number
US04603201

Reaction notes

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