Water → 4-(Methylthio)thiobenzamide

HRID 2212336Notes

Reaction equation

HRID 2212336 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 4N solution of hydrogen chloride in ethyl acetate (130 mL). To this solution was added O,O-diethyl dithiophosphate (15 mL) and the mixture was stirred at room temperature for 22 hours. Water (100 mL) was added to the reaction mixture and extracted with ethyl acetate. After the insoluble materials were filtered off, the filtrate was washed with a saturated aqueous solution of sodium chloride and dried and, thereafter, the solvent was distilled off. The residue was recrystallized from ethyl acetate to obtain 10 g of the title compound (yield 67%).

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationAfter the insoluble materials were filtered off
  3. washthe filtrate was washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-db0fd3167060484fb54d5ec92e15499f
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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