Potassium ethylxanthate → HCID 178494483, compound

HRID 1064836Notes

Reaction equation

HRID 1064836 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:9]([CH2:10][O:11][CH3:12])=[CH:8][CH:7]=[C:6]([N+:13]([O-])=O)[C:5]=1[OH:16].[C:17](=S)(OCC)[S-:18].[K+]>C(O)C>[CH3:12][O:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]2[N:13]=[C:17]([SH:18])[O:16][C:5]=2[C:4]=1[CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 22272710HCID 22272710, compound

Product 1

HCID 178494483HCID 178494483, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thus, the aminophenol (276 mg, 1.29 mmol) was dissolved in ethanol (10 ml) and potassium O-ethyl dithiocarbonate (228 mg, 1.42 mmol) was added thereto followed by heating to reflux for 16 hours. After cooling, the solvent was evaporated therefrom in vacuo. The residue was acidified by adding 2N hydrochloric acid thereto and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, hexane:acetone=5:3) to provide 182 mg (yield 59%) of 6,7-bis(methoxymethyl)-2-mercaptobenzooxazole as pale brown solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 16 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated
  5. additionby adding 2N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materiala saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by a preparative thin layer chromatography (developing solvent, hexane:acetone=5:3)

Sources & evidence

ORD record
ord-6f414ff46d7e4b589c53838c06936930
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

Loading…