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

HRID 1012216Notes

Reaction equation

HRID 1012216 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+].C(OOC1(C(C)(C)C)CCCCC1)(=O)OC1(C(C)(C)C)CCCCC1.[Cl:42]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:42])=[O:10]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehydeHCID 57031836Bis(tert-butylcyclohexyl) peroxycarbonate

Product 1

HCID 117454925-Chloro-1,3-dimethyl-1h-pyrazole-4-carbonyl chlorideYield 68%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 48 g of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde in 230 ml of chlorobenzene are added 36.5 g of sodium carbonate. Subsequently, 1.2 g of bis(tert-butylcyclohexyl) peroxycarbonate are added at 20° C. and the mixture is heated to 40° C. Within 4 hours, 24 g of chlorine gas are introduced. After the gas introduction has ended, the reaction solution is stirred at 40° C. for a further 30 minutes. The solid is filtered off and washed with a little chlorobenzene. After removal of the solvent, 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride is obtained in a yield of 68%.

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with a little chlorobenzene
  3. customAfter removal of the solvent

Sources & evidence

ORD record
ord-955abc7034944b2cadab414d8ce832f6
Source dataset
uspto-grants-2011_07
Patent number
US07977494B2

Reaction notes

Loading…