Diethyl dithiophosphate, potassium salt → HCID 86672534, compound

HRID 541310Notes

Reaction equation

HRID 541310 reaction equation
[C:1]([C:3]1[C:4]([CH3:16])=[CH:5][C:6]([CH:13]2[CH2:15][CH2:14]2)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].P(OCC)(OCC)([S-])=[S:18]>O1CCCC1.O>[C:1]([C:3]1[C:4]([CH3:16])=[CH:5][C:6]([CH:13]2[CH2:15][CH2:14]2)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])(=[S:18])[NH2:2]

Participants

5

Reactant 2

HCID 1385274Diethyl dithiophosphate, potassium saltHCID 68288710HCID 68288710, compound2×

Product 1

HCID 86672534HCID 86672534, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a round-bottom flask, was added a solution of methyl 5-cyano-2-cyclopropyl-4-methylbenzoate (compound 190.3, 220 mg, 0.920 mmol, 1.00 equiv, 90%) in tetrahydrofuran (6 mL). A solution of O,O′-diethyl dithiophosphate (300 mg, 1.61 mmol, 2.00 equiv) in water (1.5 mL) was added to the solution, and the resulting mixture was stirred overnight at 80° C. in an oil bath (CAUTION: significant gas evolution occurs—this and all other reactions described herein should be carried out in well ventilated fume hoods). After cooling to ambient temperature, the mixture was concentrated in vacuo. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (5:1) as eluent. The collected fractions were combined and concentrated in vacuo to furnish 100 mg (39%) of methyl 5-carbamothioyl-2-cyclopropyl-4-methylbenzoate as a yellow solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba838d1ca29b427992981cf7a1a2caf2
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…