Thionyl Chloride → HCID 19809473, compound

HRID 1617468Notes

Reaction equation

HRID 1617468 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.S(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>C(O)CCC>[CH2:4]([O:9][C:8](=[O:10])[C:6]1[CH:5]=[C:4]([Cl:11])[N:3]=[C:2]([Cl:1])[CH:7]=1)[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 948302,6-Dichloroisonicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 19809473HCID 19809473, compoundYield 208.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a suspension of 2,6-dichloropyridine-4-carboxylic acid (16 g) (CAS RN: [5398-44-7]) in n-butanol (150 mL) was added thionylchloride (9.1 mL) dropwise. The reaction mixture was heated to reflux for 1.5 hours, cooled to room temperature and then a saturated aqueous solution of NaHCO3 (160 mL) was added (pH˜7). The mixture was extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give 2,6-dichloro-isonicotinic acid butyl ester (21.51 g) as crude product, which was directly subjected to the next step.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. extractionThe mixture was extracted with EtOAc (2×150 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee5594371efc4263acbc1cabedebe878
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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