Phosphorus sulfide (P2S5) → O-methyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinothioate

HRID 1980454Notes

Reaction equation

HRID 1980454 reaction equation
[CH2:1]([P:3]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[Cl:24])[CH:10]=[CH:9][C:8]=1[N+:25]([O-:27])=[O:26])(=O)[O:4][CH3:5])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:29]>>[CH2:1]([P:3]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[Cl:24])[CH:10]=[CH:9][C:8]=1[N+:25]([O-:27])=[O:26])(=[S:29])[O:4][CH3:5])[CH3:2]

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 13456449methyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

Product 1

HCID 13456453O-methyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinothioate

Procedure

A mixture of methyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate (4.7 mmol) and phosphorus pentasulfide (1.2 mmol) is heated to 150°-160° under nitrogen for 3-4 hours. After cooling, the residue is purified by preparative thin-layer chromatography (on silica gel, eluting with 20% ethyl acetate/hexane) to give O-methyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinothioate.

Workup

  1. temperatureis heated to 150°-160° under nitrogen for 3-4 hours
  2. temperatureAfter cooling
  3. customthe residue is purified by preparative thin-layer chromatography (on silica gel, eluting with 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5a287462cdbd4b84be81e971b1f92454
Source dataset
uspto-grants-1985_04
Patent number
US04509970

Reaction notes

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