Potassium ethylxanthate → HCID 178504598, compound

HRID 1064852Notes

Reaction equation

HRID 1064852 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:10])=[O:9])[C:3]=1[OH:11].[C:12](=S)(OCC)[S-:13].[K+]>C(O)C>[SH:13][C:12]1[O:11][C:3]2[C:4]([S:8]([CH3:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 22272631HCID 22272631, compound

Product 1

HCID 178504598HCID 178504598, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of this aminophenol. (233 mg, 1.36 mmol) in ethanol (10 ml) was added potassium O-ethyl dithiocarbonate (300 mg, 1.87 mmol) and the mixture was stirred under heating to reflux for 9 hours. The reaction solution was acidified to pH, 4 with 1 N hydrochloric acid and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentraed in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:methanol=10:1) and recrystallized from chloroform-ether to provide 223 mg (yield 77%) of 2-mercapto-7-methansulfinylbenzoxazole as pale brown powdery crystals.

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 9 hours
  3. extraction4 with 1 N hydrochloric acid and extracted with chloroform
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:methanol=10:1)
  7. customrecrystallized from chloroform-ether

Sources & evidence

ORD record
ord-f778abbf68af4267b93f4f3e819e5f29
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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