Potassium ethylxanthate → HCID 178488033, compound

HRID 512447Notes

Reaction equation

HRID 512447 reaction equation
[O:1]([CH2:5][CH3:6])[C:2]([S-:4])=S.[K+].[NH2:8][C:9]1C=C[C:12]([O:15][CH3:16])=[CH:11][C:10]=1O>C(O)C>[SH:4][C:2]1[O:1][C:5]2[CH:6]=[C:12]([O:15][CH3:16])[CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 99421632-Amino-5-methoxyphenol

Product 1

HCID 178488033HCID 178488033, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Next, a mixture of potassium ethyl xanthate (4.6 g, 28.8 mmol) and crude 2-amino-5-methoxyphenol (4.0 g, 28.8 mmol) was dissolved in ethanol (150 mL). The mixture was heated at 80° C. overnight. After cooling, the solvent was evaporated under reduced pressure. The resultant residue was dissolved in water and treated with 1N HCl to pH 5, resulting in a precipitate, which was collected. The solid thus collected was purified by chromatography with petroleum ether/ethyl acetate (3:1 v/v) to afford 2-mercapto-6-methoxybenzoxazole (4.0 g, yield 77%).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe resultant residue was dissolved in water
  4. additiontreated with 1N HCl to pH 5
  5. customresulting in a precipitate, which
  6. customwas collected
  7. customThe solid thus collected
  8. customwas purified by chromatography with petroleum ether/ethyl acetate (3:1 v/v)

Sources & evidence

ORD record
ord-5dfd533425064c3e9349f655225d91e5
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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