Oxalyl chloride → 5-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carbonyl chloride

HRID 2400567Notes

Reaction equation

HRID 2400567 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([OH:17])=O)[CH:3]=1.C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C=O)C>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([Cl:21])=[O:17])[CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27470481-(4-Methylbenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid2×

Product 1

HCID 595047005-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboxylic acid (Intermediate B, 390 mg, 1.69 mmol), was dissolved in dichloromethane (26 mL) and cooled to 0° C. Oxalyl chloride was added (0.79 mL, 8.47 mmol) along with 1 drop of DMF. The ice bath was removed and the mixture was stirred at rt for 30 min before the solvent was evaporated. The residue was used in the next step with no further purification or characterization.

Workup

  1. customThe ice bath was removed
  2. customwas evaporated
  3. customThe residue was used in the next step with no further purification or characterization

Sources & evidence

ORD record
ord-61571747528f462a837d99fc162db6d3
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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