2-Methylphenyl isothiocyanate → HCID 53868986, compound

HRID 1372561Notes

Reaction equation

HRID 1372561 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[C:16]1([CH3:25])[C:17]([N:22]=[C:23]=S)=[CH:18][CH:19]=[CH:20][CH:21]=1>C(O)C.[Pd]>[CH3:25][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]1[O:1][C:2]2[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 691952-Methylphenyl isothiocyanateHCID 18433366HCID 18433366, compound

Product 1

HCID 53868986HCID 53868986, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In ethanol (20 ml) was dissolved methyl 3-hydroxy-4-nitrophenylacetate (1.00 g, 4.74 mmol), followed by the addition of 5% palladium/carbon (500 mg). Under stirring at room temperature, the mixture was subjected to catalytic hydrogenation for 15 hours. After filtration of the reaction mixture through Celite to remove the insoluble matter, 2-tolyl isothiocyanate (765 μl, 5.69 mmol) was added to the filtrate while stirring at room temperature. The reaction mixture was stirred for 15 hours. After addition of mercuric oxide (yellow) (1.72 g, 7.94 mmol), the mixture was heated under reflux for 5 hours under stirring. The reaction mixture was then cooled to room temperature. After filtration of the reaction mixture through Celite under reduced pressure, the solvent was distilled off under reduced pressure from the filtrate. The residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (10:1) eluate fractions, the title compound (1.18 g, 84%) was obtained as a yellow oil.

Workup

  1. filtrationAfter filtration of the reaction mixture through Celite
  2. additionwas added to the filtrate
  3. stirringwhile stirring at room temperature
  4. stirringThe reaction mixture was stirred for 15 hours
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 5 hours
  7. stirringunder stirring
  8. temperatureThe reaction mixture was then cooled to room temperature
  9. filtrationAfter filtration of the reaction mixture through Celite under reduced pressure
  10. distillationthe solvent was distilled off under reduced pressure from the filtrate
  11. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (10:1) eluate fractions

Sources & evidence

ORD record
ord-52a5d4d1408a4a2e9cdee10e3eeaf031
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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