Hydrazine hydrate (1:1) → HCID 5260620, compound

HRID 2359066Notes

Reaction equation

HRID 2359066 reaction equation
[C:1]([C:4]1[S:5][C:6]([Cl:9])=[CH:7][CH:8]=1)(=O)[CH3:2].CO[C:12](OC)([N:14](C)C)[CH3:13].O.[NH2:20]N>CN(C)C(=O)C>[Cl:9][C:6]1[S:5][C:4]([C:1]2[CH:2]=[C:12]([CH3:13])[NH:14][N:20]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 805722-Acetyl-5-chlorothiopheneHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 5260620HCID 5260620, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-acetyl-5-chlorothiophene (156 mmol) and N,N-dimethylacetamide dimethyl acetal (171 mmol) in 200 mL N,N-dimethylacetamide was heated to 90° C. for 4 h and then allowed to cool to room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in 200 mL absolute ethanol. Hydrazine monohydrate (234 mmol) was added and the mixture was stirred at room temperature for 24 h. The solvent was removed under vacuum. Petroleum ether was added and the precipitate formed was filtered then washed to afford 22 g (71% yield) 3-(5-chloro-2-thienyl)-5-methyl-1H-pyrazole.

Workup

  1. temperatureto cool to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 200 mL absolute ethanol
  4. customThe solvent was removed under vacuum
  5. additionPetroleum ether was added
  6. customthe precipitate formed
  7. filtrationwas filtered
  8. washthen washed

Sources & evidence

ORD record
ord-c96c5394755245c4929584072115aadf
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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