Dimethylformamide → 4-Trifluoromethylnicotinoyl chloride

HRID 1744280Notes

Reaction equation

HRID 1744280 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9](O)=[O:10])=[CH:7][N:6]=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O.CN(C)C=O>C1C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([Cl:16])=[O:10])=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

Product 1

HCID 117904654-Trifluoromethylnicotinoyl chlorideYield 90.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Trifluoromethylnicotinic acid (50.09 g, 0.262 mol) was suspended in benzene (250 ml), and thionyl chloride (38.2 ml, 0.524 mol) and N,N-dimethylformamide (0.1 ml) were added. The mixture was refluxed for 3 hours. The reaction mixture was concentrated, and the residue was distilled under reduced pressure to obtain 49.45 g (yield 90.1%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-8fce0577896845a1a44c780a1913314a
Source dataset
uspto-grants-2006_03
Patent number
US07015236B2

Reaction notes

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