Water → 4-(Methylthio)thiobenzamide

HRID 1062622Notes

Reaction equation

HRID 1062622 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.P([S-])(OCC)(OCC)=[S:12].O>Cl.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]([NH2:8])=[S:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5909604-(Methylthio)benzonitrileHCID 1385274Diethyl dithiophosphate, potassium salt

Product 1

HCID 30033144-(Methylthio)thiobenzamideYield 67%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methylthiobenzonitrile (12 g) was dissolved in a solution (130 mL) of 4N hydrogen chloride in ethyl acetate. To this solution was added O,O-diethyl dithiophosphate (15 mL) and the mixture was stirred at room temperature for 22 h. To the reaction mixture was added water (100 mL), and the mixture was extracted with ethyl acetate. The insoluble material was filtered off and the filtrate was washed with saturated brine, dried and the solvent was evaporated. The residue was recrystallized from ethyl acetate to give the title compound (10 g, yield 67%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. filtrationThe insoluble material was filtered off
  3. washthe filtrate was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6c2e59aec7eb4bd69241f208fea458aa
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

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