Thionyl Chloride → HCID 87427267, compound

HRID 623468Notes

Reaction equation

HRID 623468 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[N:14]=[C:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].Cl[C:22]1C=CC(C(O)=O)=C(OCC(F)(F)F)N=1.FC(F)(F)COC1N=C(OCC(F)(F)F)C=CC=1C(O)=O>CO>[Cl:5][C:6]1[N:14]=[C:13]([O:15][CH2:16][C:17]([F:20])([F:18])[F:19])[CH:12]=[CH:11][C:7]=1[C:8]([O:10][CH3:22])=[O:9]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 63376425HCID 63376425, compoundHCID 87426689HCID 87426689, compoundHCID 87427443HCID 87427443, compound

Product 1

HCID 87427267HCID 87427267, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (4.7 mL, 63.9 mmol) is added dropwise a solution of 2-chloro-6-(2,2,2-trifluoroethoxy)nicotinic acid including 6-chloro-2-(2,2,2-trifluoroethoxy)nicotinic acid and 2,6-bis(2,2,2-trifluoroethoxy)nicotinic acid (4.08 g, Step-1) in methanol (50 mL) and refluxed with stirring for 3 hours. After removal of solvent, the residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (20:1) to give 2.90 g (67% yield) of the title compound including methyl 6-chloro-2-(2,2,2-trifluoroethoxy)nicotinate as a white solid. This material is used for the next reaction (Step-3) without further purification.

Workup

  1. temperaturerefluxed
  2. customAfter removal of solvent
  3. customthe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-88ab24fdc5af444294a306318ae436f3
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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