O,O-Diethyl dithiophosphate → HCID 74390509, compound

HRID 556785Notes

Reaction equation

HRID 556785 reaction equation
[CH2:1]([O:3][P:4](=[S:9])([SH:8])[O:5][CH2:6][CH3:7])[CH3:2].Br[CH2:11][CH:12]=[CH:13][CH2:14]Br>C(O)C.O>[CH2:1]([O:3][P:4](=[S:8])([O:5][CH2:6][CH3:7])[S:9][CH2:11][CH:12]=[CH:13][CH2:14][S:9][P:4]([O:5][CH2:6][CH3:7])([O:3][CH2:1][CH3:2])=[S:8])[CH3:2]

Participants

5

Reactant 2

HCID 9274O,O-Diethyl dithiophosphateHCID 131802-Butene, 1,4-dibromo-

Product 1

HCID 74390509HCID 74390509, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the ammonium salt of dithiophosphoric acid O,O-diethyl ester (15.8 g, 78 mmol) in ethanol (130 mL) at 80° C. is added 1,4-dibromo-2-butene (7.55 g, 35 mmol) in portions. The resulting mixture is cooled, diluted with water (150 mL) and extracted with methylene chloride (3×100 mL). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to yield 15 g (99%) of S-[4-(diethoxy-thiophosphorylsulfanyl)-but-2-enyl]dithiophosphoric acid O,O′-diethyl ester, having the structure:

Workup

  1. temperatureThe resulting mixture is cooled
  2. extractionextracted with methylene chloride (3×100 mL)
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-542a7a359649400e8763e42ab5b5fbff
Source dataset
uspto-grants-2011_11
Patent number
US08058332B2

Reaction notes

Loading…