Hydrochloric Acid → methyl P-methyl-2-nitro-5-phenylthiophenylphosphinate

HRID 1388776Notes

Reaction equation

HRID 1388776 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][CH2:4]C.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+].Cl>C(O)C.O>[CH3:1][P:2]([C:7]1[CH:12]=[C:11]([S:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])(=[O:6])[O:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 53860251ethyl P-methyl-2-nitro-5-chlorophenylphosphinate

Product 1

HCID 54434247methyl P-methyl-2-nitro-5-phenylthiophenylphosphinate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of ethyl P-methyl-2-nitro-5-chlorophenylphosphinate (20.0 mmol) and thiophenol (40.0 mmol) in 20 ml of ethanol is added sodium hydroxide (60.0 mmol) in 1 ml of water. The mixture is heated under reflux for 24 hours. The reaction mixture is poured into water, acidified with dilute HCl and extracted with methylene chloride (2X). The combined extracts are washed with brine, dried and evaporated to dryness. The resulting oily residue is treated with diazomethane in methanol, concentrated and purified by preparative TLC to yield methyl P-methyl-2-nitro-5-phenylthiophenylphosphinate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with methylene chloride (2X)
  4. washThe combined extracts are washed with brine
  5. customdried
  6. customevaporated to dryness
  7. additionThe resulting oily residue is treated with diazomethane in methanol
  8. concentrationconcentrated
  9. custompurified by preparative TLC

Sources & evidence

ORD record
ord-93251f968b4843029c80987859c61651
Source dataset
uspto-grants-1984_02
Patent number
US04433149

Reaction notes

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