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

HRID 1284419Notes

Reaction equation

HRID 1284419 reaction equation
[CH3:1][P:2]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[Cl:23])[CH:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])(=O)[O:3][CH3:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:28]>>[CH3:1][P:2]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[Cl:23])[CH:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])(=[S:28])[O:3][CH3:4]

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 13564436methyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

Product 1

HCID 70456176methyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinothioate

Procedure

A mixture of methyl P-methyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate (1.5 g, 4.7 mmol) and phosphorus pentasulfide (0.52 g, 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 methyl P-methyl-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-3d6535f9baa142a3befb0556debd161b
Source dataset
uspto-grants-1986_01
Patent number
US04563310

Reaction notes

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