Dimethylformamide → 1-(3-Bromophenyl)-5-methyl-1h-pyrazole-3-carboxamide

HRID 733123Notes

Reaction equation

HRID 733123 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][C:10](C(O)=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:16]([O-])(=O)C.[NH4+].C[N:22]([CH:24]=[O:25])C>>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:16])=[CH:11][C:10]([C:24]([NH2:22])=[O:25])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 431246391-(3-Bromophenyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 574282521-(3-Bromophenyl)-5-methyl-1h-pyrazole-3-carboxamideYield 82%

Procedure

To a solution of the carboxylic acid (3.79 g, 14.1 mmol) in DMF (47 ml) was added 1,1-carbonyldiimidazole (3.45 g, 21.2 mmol) and the mixture was stirred at room temperature for 3 hours. Anhydrous ammonium acetate (10.9 g, 141 mmol) was then added and the reaction was stirred at room temperature for an additional 16 hours. The reaction mixture was partitioned between ethylacetate and saturated sodium bicarbonate. The organic phase was washed with water, brine, then dried over sodium sulfate and concentrated. The crude product obtained was purified by silica-gel column chromatography (2:3 hexanes/ethyl acetate) to give the product as a white solid (3.23 g, 82%).

Workup

  1. stirringthe reaction was stirred at room temperature for an additional 16 hours
  2. customThe reaction mixture was partitioned between ethylacetate and saturated sodium bicarbonate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customwas purified by silica-gel column chromatography (2:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5998c582096346eab508f7f01d9c7082
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

Loading…