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

HRID 463556Notes

Reaction equation

HRID 463556 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 (2×). 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 (2×)
  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-9be7aedd1afd4fbb8d7420ed4e565160
Source dataset
uspto-grants-1985_05
Patent number
US04520197

Reaction notes

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