Thionyl Chloride → 2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride

HRID 2111901Notes

Reaction equation

HRID 2111901 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][N:6]1[C:10]([C:11](O)=[O:12])=[CH:9][C:8]([CH3:14])=[N:7]1>CN(C)C=O>[CH3:5][N:6]1[C:10]([C:11]([Cl:3])=[O:12])=[CH:9][C:8]([CH3:14])=[N:7]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5877211,3-Dimethyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Thionyl chloride (1.04 ml, 14.4 mmol) is added to a stirred solution of 1,3-dimethyl-1H-pyrazole-5-carboxylic acid (0.5 g, 3.6 mmol) and dimethylformamide (3 drops). The reaction is stirred for 2 hours at room temperature and then for 2 hours at 80° C. The reaction is concentrated. The residue is dissolved in dichloromethane and then the solvent is evaporated to yield 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride.

Workup

  1. waitfor 2 hours at 80° C
  2. concentrationThe reaction is concentrated
  3. dissolutionThe residue is dissolved in dichloromethane
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-78e1e3a54a22450a9eeb0920906dbd71
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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