Thionyl Chloride → 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

HRID 251892

Reaction equation

HRID 251892 reaction equation
[CH3:1][N:2]1[C:6]([C:7](O)=[O:8])=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.S(Cl)([Cl:16])=O>CCCCCC>[CH3:1][N:2]1[C:6]([C:7]([Cl:16])=[O:8])=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6065401-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 147706071-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chlorideYield 67.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 0.19 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid, 0.15 g of thionyl chloride and 5 ml of hexane was heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain 0.14 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride. To a mixture of 0.22 g of N-(2-aminobenzoyl)-N′-ethoxycarbonylhydrazine and 10 ml of pyridine was added 0.14 g of the resulting 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and a deposited precipitates were collected by filtration to obtain 0.23 g of the present compound (3) of the formula:

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b24769a02e44359ace18dc0fe119baf
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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