Diethyl dithiophosphate, potassium salt → HCID 71695284, compound

HRID 541209

Reaction equation

HRID 541209 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].P(OCC)(OCC)([S-])=[S:15]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7])(=[S:15])[NH2:2]

Participants

4

Reactant 2

HCID 1385274Diethyl dithiophosphate, potassium saltHCID 11819538Methyl 3-cyano-4-methylbenzoate2×

Product 1

HCID 71695284HCID 71695284, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of methyl 3-cyano-4-methylbenzoate (compound 1.7, 880 mg, 5.02 mmol, 1.00 equiv) and O,O′-diethyl dithiophosphate (1.41 g, 8.29 mmol, 1.50 equiv) in THF/H2O (40 mL) was stirred at 80° C. (CAUTION: significant gas evolution occurs—this and all other reactions described herein should be carried out in well ventilated fume hoods). After 3 h, the organic solvent was removed under reduced pressure and the residual aqueous phase was extracted with 3×20 mL of ethyl acetate. The combined organic layers were concentrated under reduced pressure to yield 0.85 g (79%) of the title compound as a light yellow solid.

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. extractionthe residual aqueous phase was extracted with 3×20 mL of ethyl acetate
  3. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc3a1f2f247648e5844296f821f11e8f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Linked notes

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