Potassium ethylxanthate → HCID 178509644, compound

HRID 1022769

Reaction equation

HRID 1022769 reaction equation
[NH2:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O[C:14]([S-])=[S:15])C.[K+]>N1C=CC=CC=1>[SH:15][C:14]1[O:10][C:9]2[C:2](=[C:3]([C:4]#[N:5])[CH:6]=[CH:7][CH:8]=2)[N:1]=1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 159063362-Amino-3-hydroxybenzonitrile

Product 1

HCID 178509644HCID 178509644, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-3-hydroxybenzonitrile (298 mg) and potassium ethylxanthate (427 mg) in pyridine (7.4 ml) was heated under reflux for 3 hr. To the reaction mixture was added distilled water, the mixture was acidified with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (178 mg).

Workup

  1. temperatureunder reflux for 3 hr
  2. additionTo the reaction mixture was added
  3. distillationdistilled water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with distilled water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-10ea5d5ffe4d4cfdbb2aa24469c0957c
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Linked notes

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