Potassium ethylxanthate → HCID 178488033, compound

HRID 512441Notes

Reaction equation

HRID 512441 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].O(CC)[C:12]([S-])=[S:13].[K+]>C(O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:12]([SH:13])[O:10][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 99421632-Amino-5-methoxyphenol

Product 1

HCID 178488033HCID 178488033, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Next, a mixture of 2-amino-5-methoxyphenol (3c) (6.03 g, 43.33 mmol) and potassium ethyl xanthate (6.95 g, 73.33 mmol) in ethanol (80 mL) was heated at reflux for 18 h. The reaction was subsequently cooled and the solvent was removed in vacuo. The residue was taken up in ethyl acetate (150 mL), washed successively with 4N HCl, water, and brine. The organic solution was subsequently dried over Na2SO4. After filtration to remove the drying aid, the solvent was evaporated to give 6.23 g (79%) of 6-methoxybenzoxazole-2-thiol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction was subsequently cooled
  4. customthe solvent was removed in vacuo
  5. washwashed successively with 4N HCl, water, and brine
  6. dry with materialThe organic solution was subsequently dried over Na2SO4
  7. filtrationAfter filtration
  8. customto remove the drying aid
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-801b0f9c89dd43aa838e962e50bb699e
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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