Dimethylformamide → 6-(Trifluoromethyl)nicotinoyl chloride

HRID 926444Notes

Reaction equation

HRID 926444 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][N:4]=1.CN(C=O)C.C(Cl)(=O)C([Cl:22])=O>ClCCl>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:22])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27775516-(Trifluoromethyl)nicotinic acid

Product 1

HCID 27775576-(Trifluoromethyl)nicotinoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1 L 3-neck flask equipped with an overhead stirrer, Claisen adaptor, nitrogen bubbler, 60 mL addition funnel, and thermocouple was added 6-(trifluoromethyl)nicotinic acid (45 g, 235.5 mmol), dichloromethane (540 mL) and DMF (0.910 mL, 11.77 mmol) via syringe. To this solution was added oxalyl chloride (24.51 mL, 282.56 mmol) and the reaction was allowed to stir at ambient temperature overnight. The reaction was then filtered and the clear filtrate was condensed in vacuo to afford the title compound as a brownish semisolid.

Workup

  1. customTo a 1 L 3-neck flask equipped with an overhead stirrer
  2. additionClaisen adaptor, nitrogen bubbler, 60 mL addition funnel
  3. filtrationThe reaction was then filtered
  4. customcondensed in vacuo

Sources & evidence

ORD record
ord-594263973b864c20bc27151900bb0281
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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