Hydrochloric Acid → 2-(3-Trifluoromethylphenoxy)nicotinoyl chloride

HRID 1679795Notes

Reaction equation

HRID 1679795 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10].S(Cl)([Cl:23])=O.Cl>Cl.C(N(CC)CC)C.C(Cl)(Cl)Cl>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([Cl:23])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 2158912-(3-(Trifluoromethyl)phenoxy)-3-pyridinecarboxylic acid

Product 1

HCID 111624242-(3-Trifluoromethylphenoxy)nicotinoyl chlorideYield 66.7%

Reagents, catalysts & solvents 2

HCID 11130Triethylamine hydrochlorideCatalystHCID 6212ChloroformSolvent

Procedure

There were combined 14.1 grams (0.05 mole) 2-(3-trifluoromethylphenoxy) nicotinic acid, 0.1 grams triethylamine hydrochloride and 150 milliliters of chloroform. The mixture was stirred and heated to reflux. Then, 6.5 grams (0.055 mole) thionyl chloride was slowly added. After addition was complete the reaction mass was heated under reflux until hydrogen chloride evolution had ceased (about 30 minutes); it was then cooled to room temperature, filtered, and the solvent removed under vacuum producing 10.0 grams (66.7% of theoretical yield) of 2-(3-trifluoromethylphenoxy) nicotinoyl chloride. The structure was confirmed by infrared spectral analysis.

Workup

  1. temperatureheated to reflux
  2. additionAfter addition
  3. temperaturewas heated
  4. custom(about 30 minutes)
  5. filtrationfiltered
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-b81b271bd2ce46ef871e7f8dc7d735e5
Source dataset
uspto-grants-1981_06
Patent number
US04270946

Reaction notes

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