Acetonitrile → HCID 18317564, compound

HRID 1700682Notes

Reaction equation

HRID 1700682 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][C:4](=[O:15])[CH:3]=1.[C:16]1([N:22]=[C:23]=S)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(#[N:27])C>>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[NH:1][N:27]=[C:23]([NH:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:3]=2[C:4](=[O:15])[CH2:5]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7673Phenyl IsothiocyanateHCID 98593161-Amino-5-(2-chlorophenyl)cyclohexen-3-one

Product 1

HCID 18317564HCID 18317564, compound

Procedure

To a solution of 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (2.0 g) in acetonitrile (50 ml) was added phenyl isothiocyanate (1.2 g), and the mixture was refluxed for 15 hours. Under reduced pressure, the solvent was evaporated, and to the residue were added ethanol (20 ml) and hydrazine hydrate (0.55 g). The mixture was refluxed for 1 hour, and under reduced pressure, the solvent was evaporated. The residue was washed with ethyl acetate to give yellow crystals of 6-(2-chlorophenyl)-3-phenylamino-4,5,6,7-tetrahydroindazol-4-one (0.8 g).

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue were added ethanol (20 ml) and hydrazine hydrate (0.55 g)
  4. temperatureThe mixture was refluxed for 1 hour
  5. customunder reduced pressure, the solvent was evaporated
  6. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-14781bf05fc445369317120c1c54ecf5
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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