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

HRID 1012219Notes

Reaction equation

HRID 1012219 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[Cl:11]Cl>ClC1C=CC=CC=1>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([Cl:11])=[O:10]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

Product 1

HCID 117454925-Chloro-1,3-dimethyl-1h-pyrazole-4-carbonyl chlorideYield 87%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 48 g of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde in 230 ml of chlorobenzene under protective gas, 19.2 g of chlorine gas are introduced while illuminating with a mercury lamp at 30° C. within 4 hours. After the gas introduction has ended, the reaction solution is stirred with illumination at 30° C. for a further 20 minutes. The reaction solution is cooled to 5° C. and the solid is filtered off and washed with a little chlorobenzene. After the solvent has been removed, 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride is obtained in a yield of 87%.

Workup

  1. customwhile illuminating with a mercury lamp at 30° C. within 4 hours
  2. temperatureThe reaction solution is cooled to 5° C.
  3. filtrationthe solid is filtered off
  4. washwashed with a little chlorobenzene
  5. customAfter the solvent has been removed

Sources & evidence

ORD record
ord-959156777dad4a9bb40124c089b2ce15
Source dataset
uspto-grants-2011_07
Patent number
US07977494B2

Reaction notes

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