Hydrazine hydrate (1:1) → HCID 10199104, compound

HRID 395921Notes

Reaction equation

HRID 395921 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[C:12]#[C:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1>C(O)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[NH:3][N:2]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13360982HCID 13360982, compound

Product 1

HCID 10199104HCID 10199104, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 702EthanolSolvent

Procedure

Hydrazine hydrate (228 mg, 4.6 mM) and pyridinium p-toluenesulfonate (50 mg) were added to a solution of 1-(4-chlorophenyl)-3-(2-thienyl)-2-propyn-1-one (750 mg, 3.0 mM) in ethanol (30 ml), and this mixture was heated under reflux for 2 hours. After the mixture was allowed to cool to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in ethyl acetate (50 ml). This solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain 634 mg of 3-(4-chlorophenyl)-5-(2-thienyl)-1H-pyrazole, m.p. 217° C., in an 80% yield.

Workup

  1. temperaturethis mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe resulting residue was dissolved in ethyl acetate (50 ml)
  5. washThis solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  7. distillationThereafter, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-16672854e8c643fb87fb9437dbc1d43f
Source dataset
uspto-grants-2003_08
Patent number
US06605730B2

Reaction notes

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