Hydrogen Sulfide → HCID 135741556, compound

HRID 734407Notes

Reaction equation

HRID 734407 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].[SH2:12].C(NCC)C>CN(C=O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[S:12])[NH2:7])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8021DiethylamineHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 135741556HCID 135741556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-hydroxy-3-methoxybenzonitrile (15.0 g, 0.1 mol) in DMF (150 mL) was treated with a slow flow of gaseous hydrogen sulfide for 30 minutes at rt. Diethyl amine (15.6 mL, 11.0 g, 0.15 mol) was added and the solution was heated at 70° C. for 4 h. The solution was cooled to rt and the residual H2S was removed by passing argon through the solution for 30 minutes. The solvent was evaporated under reduced pressure and the residue was filtered through a plug of silica, followed by washing with EtOAc. Removal of the solvent resulted in a crude brown oil, which was used in the next step without further purification.

Workup

  1. temperatureThe solution was cooled to rt
  2. customthe residual H2S was removed
  3. customfor 30 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationthe residue was filtered through a plug of silica
  6. washby washing with EtOAc
  7. customRemoval of the solvent
  8. customresulted in a crude brown oil, which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-b059d7c780644f008ab95eb342d684c7
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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