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

HRID 1012215Notes

Reaction equation

HRID 1012215 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].C(=O)([O-])[O-].[Na+].[Na+].[Cl:17]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:17])=[O:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

Product 1

HCID 117454925-Chloro-1,3-dimethyl-1h-pyrazole-4-carbonyl chlorideYield 74%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 48.5 g of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde in 230 ml of chlorobenzene are added 36 g of sodium carbonate. Subsequently, 3.9 g of 2,2-azoisobutyronitrile (AIBN) are added at 60° C., and, within 4 hours, 24 g of chlorine gas are introduced and a further 6 g of AIBN are added. After the gas introduction has ended, the reaction solution is stirred for a further 30 minutes. 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 74%.

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with a little chlorobenzene
  3. customAfter the solvent has been removed

Sources & evidence

ORD record
ord-ff3d0cfa89bf43d38cc4324d77036c5a
Source dataset
uspto-grants-2011_07
Patent number
US07977494B2

Reaction notes

Loading…