Thionyl Chloride → 2-Methyl-6-(trifluoromethyl)nicotinoyl chloride

HRID 1391649Notes

Reaction equation

HRID 1391649 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9]>C1(C)C=CC=CC=1>[CH3:5][C:6]1[C:7]([C:8]([Cl:3])=[O:9])=[CH:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27756832-Methyl-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 27756752-Methyl-6-(trifluoromethyl)nicotinoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (4.35 g, 36.5 mmol) was added to a mixture of 2-methyl-6-trifluoromethyl nicotinic acid (5.00 g, 24.4 mmol) in 75 mL of toluene and the mixture was heated at reflux for 3 hours. The reaction was cooled to room temperature and the solvent was removed under reduced pressure. Excess thionyl chloride was removed by azeotrope with toluene. The resultant acid chloride was used as is in Example 4, Step B.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe solvent was removed under reduced pressure
  4. customExcess thionyl chloride was removed by azeotrope with toluene

Sources & evidence

ORD record
ord-292669329be041e58347e6c40fe1f5c5
Source dataset
uspto-grants-2008_03
Patent number
US07338978B2

Reaction notes

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