Potassium Acetate → 1-Acetyl-1H-thieno[2,3-c]pyrazole-5-carbonitrile

HRID 34074

Reaction equation

HRID 34074 reaction equation
Cl[C:2]1[S:3][C:4]([C:13]#[N:14])=[CH:5][C:6]=1[CH:7]=[N:8][NH:9][C:10](=[O:12])[CH3:11].C([O-])(=O)C.[K+]>C1(OC2C=CC=CC=2)C=CC=CC=1.[Cu]>[C:10]([N:9]1[C:2]2[S:3][C:4]([C:13]#[N:14])=[CH:5][C:6]=2[CH:7]=[N:8]1)(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 68929248Acetic acid (2-chloro-5-cyanothiophen-3-ylmethylene)hydrazide

Product 1

HCID 689272371-Acetyl-1H-thieno[2,3-c]pyrazole-5-carbonitrileYield 10.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 2.53 g of acetic acid (2-chloro-5-cyanothiophen-3-ylmethylene)hydrazide in 22 mL of diphenyl ether were added copper powder and potassium acetate at room temperature, and stirred at 200° C. for 6 hours. Following filtration through Celite, the filtrate was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5), to afford 215 mg of the title compound as colorless crystals.

Workup

  1. filtrationfiltration through Celite
  2. washthe filtrate was washed successively with saturated aqueous ammonium chloride and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5)

Sources & evidence

ORD record
ord-9364f7cbd9224c62904bb2461f3a280e
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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