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

HRID 1413649Notes

Reaction equation

HRID 1413649 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 663%

Reagents, catalysts & solvents 2

HCID 11130Triethylamine hydrochlorideCatalystHCID 6212ChloroformSolvent

Procedure

There are mixed 14.1 grams (0.05 mole) of the acid from step (a), 0.1 grams triethylamine hydrochloride and 150 milliliters chloroform, followed by stirring and heating to reflux. Then 6.5 grams (0.055 mole) thionyl chloride was slowly added, dropwise. After the addition was complete, the reaction mass was heated under reflux until evolution of HCl had ceased (about 30 minutes). The reaction mixture was cooled to room temperature, and the solvent was removed by vacuum distillation yielding 100 grams (66.7% of theoretical yield) of 2-(3-trifluoromethylphenoxy) nicotinoyl chloride.

Workup

  1. temperatureheating to reflux
  2. additionAfter the addition
  3. temperaturethe reaction mass was heated
  4. custom(about 30 minutes)
  5. customthe solvent was removed by vacuum distillation

Sources & evidence

ORD record
ord-c2b3c1437eac48238dcf60aa93bd6d6a
Source dataset
uspto-grants-1981_02
Patent number
US04251263

Reaction notes

Loading…