Hydrazine hydrate (1:1) → HCID 178431894, compound

HRID 2359063Notes

Reaction equation

HRID 2359063 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[S:8][CH:9]=[C:10]([CH3:12])[CH:11]=1)=O.O.[NH2:15]N>C(O)C>[CH3:12][C:10]1[CH:11]=[C:7]([C:5]2[CH:4]=[CH:3][NH:2][N:15]=2)[S:8][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 672605793-(Dimethylamino)-1-(4-methyl-2-thienyl)prop-2-en-1-one

Product 1

HCID 178431894HCID 178431894, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(4-methyl-2-thienyl)prop-2-en-1-one (72 mmol) and hydrazine hydrate (144 mmol) in 80 mL ethanol was refluxed for 18 h and then allowed to cool to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was successively washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and brine, dried over MgSO4, filtered and concentrated to afford 11.58 g (98% yield) 3-(4-methyl-2-thienyl)-1H-pyrazole which was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was successively washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e636b33a7ead4dec82cefb468e76d26e
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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