Dimethylformamide → 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride

HRID 1748610

Reaction equation

[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([OH:19])=O.CN(C)C=O.S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([Cl:27])=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid (40.0 g) described in Reference Example 8 in toluene (147 ml) were added N,N-dimethylformamide (catalyst quantity) and thionyl chloride (52.6 g) at room temperature, and stirred at 80° C. for 4.5 hours. After completion of the reaction, the solvent and excessive thionyl chloride were evaporated, azeotropy was performed with toluene twice, and then dried in vacuo to give the titled compound as a pale yellow solid.

Workup

customAfter completion of the reaction
customthe solvent and excessive thionyl chloride were evaporated
customdried in vacuo

Sources & evidence

ORD record: ord-5ee31dcb134e4a2ab06647809297759a
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Linked notes

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