HCID 19099699, compound → HCID 86747569, compound

HRID 1975341Notes

Reaction equation

HRID 1975341 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8]([O-:10])=[O:9])([O:5][CH3:6])=[O:4].[K+].Br[CH2:13][N:14]1[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([Cl:23])[C:16]([C:24]#[N:25])=[C:15]1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1>CN(C)C=O.O>[CH3:1][O:2][P:3]([CH2:7][C:8]([O:10][CH2:13][N:14]1[C:15]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:16]([C:24]#[N:25])[C:17]([Cl:23])=[C:18]1[C:19]([F:22])([F:20])[F:21])=[O:9])([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 19099699HCID 19099699, compoundHCID 23663227Potassium (dimethoxyphosphoryl)acetate

Product 1

HCID 86747569HCID 86747569, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of potassium (dimethylphosphono)acetate (0.69 g, 4 mmol) in N,N-dimethylformamide is treated with 1-(bromomethyl)-4-chloro-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (0.79 g, 2 mmol), stirred at room temperature for one hour, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous MgSO4 and concentrated in vacuo to obtain a brown oil. The oil is chromatographed using silica gel and a 1:1 hexanes/ethyl acetate mixture to give the title product as a viscous yellow oil (0.41 g) which is identified by 13C and 19FNMR spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed sequentially with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customto obtain a brown oil
  6. customThe oil is chromatographed

Sources & evidence

ORD record
ord-f783a1bfb2574974886571554b5ea17c
Source dataset
uspto-grants-1994_02
Patent number
US05286741

Reaction notes

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