Hydrazine hydrate (1:1) → HCID 178419472, compound

HRID 2359061Notes

Reaction equation

HRID 2359061 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7](=O)[CH:8]=[CH:9][N:10](C)C)[S:5][CH:6]=1.O.[NH2:15]N>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:7]2[CH:8]=[CH:9][NH:10][N:15]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260953HCID 67260953, compound

Product 1

HCID 178419472HCID 178419472, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-bromo-2-thienyl)-3-(dimethylamino)prop-2-en-1-one (43.5 mmol) and hydrazine hydrate (86.9 mmol) in 50 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 9.74 g (94% yield) 3-(4-bromo-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-041f37067fff4cb69d7cca833bda16e7
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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