Potassium ethylxanthate → HCID 178424905, compound

HRID 1064854Notes

Reaction equation

HRID 1064854 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH:9]([CH3:11])[CH3:10])[C:3]=1[OH:12].[C:13](=S)(OCC)[S-:14].[K+]>C(O)C>[CH:9]([C:4]1[C:3]2[O:12][C:13]([SH:14])=[N:1][C:2]=2[C:7]([CH3:8])=[CH:6][CH:5]=1)([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 3020287HCID 3020287, compound

Product 1

HCID 178424905HCID 178424905, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro-6-isopropyl-3-methyl-2-nitrophenol (1.82 g, 7.92 mmol) obtained in Example 97 in ethanol (40 ml) was added 10% palladium carbon catalyst (1.8 g) and the mixture was stirred under hydrogen atmosphere at 60° C. for 3 hours. After the reaction was over, the reaction solution was filtered with celite and the filtrate was concentrated to provide 1.60 g of 2-amino-6-isopropyl-3-methylphenol (yield 99%) as pale brown solid. To a solution of this aminophenol (1.65 g, 7.92 mmol) in ethanol (25 ml) was added potassium O-ethyl dithiocarbonate (1.52 g, 9.50 mmol) and the mixture was heated to reflux for 8 hours and the solvent was evaporated. The resulting residue was dissolved in water, acidified to pH, 3-4 with 2 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, a saturated sodium chloride solution successively, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was crystallized from ethyl acetate-hexane to provide 0.99 g (yield 60%) of 7-isopropyl-2-mercapto-4-methylbenzoxazole as pale yellow needles.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 hours
  3. customthe solvent was evaporated
  4. dissolutionThe resulting residue was dissolved in water
  5. extraction3-4 with 2 N hydrochloric acid and extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride solution successively, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-cb0150062fd845a7bbb38ff6ae054de8
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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