Sulfuryl chloride → 5-Chloro-1,3-dimethyl-1h-pyrazole-4-carbonyl chloride

HRID 1012220Notes

Reaction equation

HRID 1012220 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=1[CH:14]=[O:15]>ClC1C=CC=CC=1Cl>[Cl:6][C:7]1[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=1[C:14]([Cl:4])=[O:15]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

Product 1

HCID 117454925-Chloro-1,3-dimethyl-1h-pyrazole-4-carbonyl chlorideYield 72%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Simultaneously, 68 g of sulphuryl chloride and 70.5 g of a 2.5% solution of 2,2-azoisobutyronitrile (AIBN) are added dropwise at 80° C. to 300 g of a 22.7% solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde in 1,2-dichlorobenzene within 4 hours. After the metered addition has ended, the reaction solution is stirred for a further 2 hours. After removal of the solvent, 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride is obtained in a yield of 72%.

Workup

  1. additionAfter the metered addition
  2. customAfter removal of the solvent

Sources & evidence

ORD record
ord-80fa4179ae2c4ba594ab6d9900819551
Source dataset
uspto-grants-2011_07
Patent number
US07977494B2

Reaction notes

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