Ammonia → HCID 67343043, compound

HRID 1910843Notes

Reaction equation

HRID 1910843 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19](O)=[O:20])[CH:16]=[N:15]2)=[CH:11][CH:10]=1.[NH3:24].O>CN(C=O)C.C(Cl)Cl>[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19]([NH2:24])=[O:20])[CH:16]=[N:15]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 65578Oxalyl chlorideHCID 435653621-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylic acid

Product 1

HCID 67343043HCID 67343043, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

According to Scheme 1 Step 3: Oxalyl chloride (227 mmol, 19.5 mL) and three drops of DMF were added to a solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylic acid (114 mmol, 26.4 g) in DCM (227 mL). The reaction mixture was stirred for 30 minutes at room temperature. After evaporation of the solvent, dry DCM (100 mL) was added to the crude residue. The acyl chloride solution was then added at 0° C. to a solution of ammonia in water (454 mmol, 23.4 g) and the reaction mixture was stirred overnight. After filtration and evaporation to dryness, 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxamide (109 mmol, 25.1 g, 96%) was obtained as a colorless solid. The crude product was used without further purification.

Workup

  1. customAfter evaporation of the solvent, dry DCM (100 mL)
  2. additionwas added to the crude residue
  3. stirringthe reaction mixture was stirred overnight
  4. filtrationAfter filtration and evaporation to dryness

Sources & evidence

ORD record
ord-68bc050ceba342ac84e55ce82bc8b64f
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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