Sodium Hydroxide → HCID 58127823, compound

HRID 1257442Notes

Reaction equation

HRID 1257442 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)#[N:2].P([S-])(OCC)(OCC)=[S:15].C(=O)([O-])O.[Na+].[OH-].[Na+]>C(OCC)(=O)C.Cl>[NH2:2][C:1](=[S:15])[CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 848548Methyl 4-(cyanomethyl)benzoateHCID 1385274Diethyl dithiophosphate, potassium salt

Product 1

HCID 58127823HCID 58127823, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

To methyl 4-(cyanomethyl)benzoate (5.0 g, 28.5 mmol) were added 4M hydrogen chloride-ethyl acetate solution (50 mL) and O,O-diethyl dithiophosphate (6.70 mL, 40.0 mmol), and the mixture was stirred overnight. The reaction mixture was alkalified with saturated aqueous sodium hydrogen carbonate solution and 8N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over sodium sulfate, and filtered by basic silica gel. The filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate-tetrahydrofuran-hexane to give the title compound (4.46 g, 75%) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered by basic silica gel
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customrecrystallized from ethyl acetate-tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-a1ae36a4d4574c2d9f945527f915ee07
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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