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

HRID 1263182Notes

Reaction equation

HRID 1263182 reaction equation
[CH2:1]([P:3]([C:14]1[CH:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[Cl:31])[CH:17]=[CH:16][C:15]=1[N+:32]([O-:34])=[O:33])(=O)[O:4][CH2:5][O:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:36]>>[CH2:1]([P:3]([C:14]1[CH:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[Cl:31])[CH:17]=[CH:16][C:15]=1[N+:32]([O-:34])=[O:33])(=[S:36])[O:4][CH2:5][O:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:2]

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 155898042,2-dimethylpropionyloxymethyl P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinate

Product 1

HCID 53712337O-(2,2-dimethylpropionyloxymethyl) P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinothioate

Procedure

A mixture of 2,2-dimethylpropionyloxymethyl 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 prep. TLC (20% ethyl acetate/hexane) to give O-(2,2-dimethylpropionyloxymethyl) 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 prep

Sources & evidence

ORD record
ord-356ec5df84544adb8638c665d72de3e9
Source dataset
uspto-grants-1984_06
Patent number
US04456465

Reaction notes

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