Potassium Carbonate → 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxamide

HRID 639972Notes

Reaction equation

HRID 639972 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1)=[O:4].[N+:13]([C:16]1[C:17]([C:21]([NH2:23])=[O:22])=[N:18][NH:19][CH:20]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:12][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:19]2[CH:20]=[C:16]([N+:13]([O-:15])=[O:14])[C:17]([C:21]([NH2:23])=[O:22])=[N:18]2)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23889312-chloro-N-(3-fluorophenyl)acetamideHCID 178513854HCID 178513854, compound

Product 1

HCID 686400711-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-N-(3-fluorophenyl)acetamide (0.65 g, 3.46 mmol), 4-nitro-1H-pyrazole-3-carboxamide (0.54 g, 3.46 mmol) and potassium carbonate (0.57 g, 4.13 mmol) in dimethylformamide (10 ml) was stirred at room temperature for 48 hours. The mixture was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was separated, washed, dried and then concentrated to yield 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxamide (730 mg, 69% yield).

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63d60955f06141bf81f005c351f3162d
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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