Benzoyl isothiocyanate → HCID 178514162, compound

HRID 908172Notes

Reaction equation

HRID 908172 reaction equation
N1C=CC(N)=N1.C(N=C=S)(=O)C1C=CC=CC=1.C([NH:26][C:27]([NH:29][C:30]1[CH:34]=[CH:33][NH:32][N:31]=1)=[S:28])(=O)C1C=CC=CC=1>CN(C=O)C>[NH:32]1[CH:33]=[CH:34][C:30]([NH:29][C:27]([NH2:26])=[S:28])=[N:31]1

Participants

5

Reactant 3

HCID 68284Benzoyl isothiocyanateHCID 178418806HCID 178418806, compoundHCID 178523937HCID 178523937, compound

Product 1

HCID 178514162HCID 178514162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1H-Pyrazol-3-ylamine (9.5 g, 114 mmol) is added to a stirred solution of benzoyl isothiocyanate (19.6 g, 120 mmol) in DMF (100 ml) at room temperature. The solution is heated at 100° C. for 30 minutes, allowed to cool and poured onto water (1000 ml). The yellow suspension of 1-benzoyl-3-(1H-pyrazol-3-yl)-thiourea is removed by filtration and washed with water. This material is dissolved in 2M aqueous sodium hydroxide (120 ml) and the solution is heated at reflux for 30 minutes. After cooling to room temperature the solution is brought to pH 4 by addition of 3M aqueous HCl and extracted with ethyl acetate. The organic extract is dried (MgSO4) and concentrated to afford the titled compound which is removed by filtration and recrystallised from dichloromethane.

Workup

  1. temperatureto cool
  2. additionpoured onto water (1000 ml)
  3. customis removed by filtration
  4. washwashed with water
  5. dissolutionThis material is dissolved in 2M aqueous sodium hydroxide (120 ml)
  6. temperaturethe solution is heated
  7. temperatureat reflux for 30 minutes
  8. temperatureAfter cooling to room temperature the solution
  9. additionis brought to pH 4 by addition of 3M aqueous HCl
  10. extractionextracted with ethyl acetate
  11. extractionThe organic extract
  12. dry with materialis dried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-b333f8628ea0400bb48750a21692a081
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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