Ethanethiol → P-methyl-2-nitro-5-ethylthiophenylphosphinic acid

HRID 463554Notes

Reaction equation

HRID 463554 reaction equation
[CH3:1][P:2]([C:7]1[CH:12]=[C:11](Cl)[CH:10]=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])(=[O:6])[O:3]CC.[CH2:17]([SH:19])[CH3:18].[OH-].[Na+]>CS(C)=O.O>[CH3:1][P:2]([C:7]1[CH:12]=[C:11]([S:19][CH2:17][CH3:18])[CH:10]=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])(=[O:6])[OH:3]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 14798Sodium HydroxideHCID 53860251ethyl P-methyl-2-nitro-5-chlorophenylphosphinate

Product 1

HCID 131713408P-methyl-2-nitro-5-ethylthiophenylphosphinic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl P-methyl-2-nitro-5-chlorophenylphosphinate (20.0 mmol) and ethanethiol (60.0 mmol) in dimethylsulfoxide (20 ml) is added a solution of sodium hydroxide (40.0 mmol) in 1 ml of water. The mixture is warmed to 60° overnight, after which it is poured into water and extracted with ether. The aqueous solution is acidified, extracted with methylene chloride, dried and evaporated to give P-methyl-2-nitro-5-ethylthiophenylphosphinic acid, which is then treated with diazomethane in methanol to give methyl P-methyl-2-nitro-5-ethylthiophenylphosphinate.

Workup

  1. temperatureThe mixture is warmed to 60° overnight
  2. extractionextracted with ether
  3. extractionextracted with methylene chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-88c77932d5a04516a556342bca9355b0
Source dataset
uspto-grants-1985_05
Patent number
US04520197

Reaction notes

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