Thionyl Chloride → HCID 23028696, compound

HRID 748716Notes

Reaction equation

HRID 748716 reaction equation
[F:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[Na+].C([O-])(=O)C.[K+]>C(O)CCC.C(Cl)(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH2:8][C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 517044Potassium AcetateHCID 147614612-Fluoro-3-(hydroxymethyl)pyridineHCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 23028696HCID 23028696, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Procedure

A chloroform (10 ml) solution of (2-fluoropyridin-3-yl)methanol (49 mg, 0.385 mmol) and thionyl chloride (0.14 ml, 1.93 mmol) was stirred at 50° C. for 3.5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was dissolved in butanol (5 ml), followed by the addition of sodium 4-chlorobenzenesulfinate (92 mg, 0.462 mmol) and potassium acetate (76 mg, 0.770 mmol). The mixture was stirred at 70 to 80° C. for 12 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, and then, dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure, whereby the title compound (59 mg, 54%) was obtained as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionEthyl acetate was added to the residue
  6. washthe mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe fraction obtained from the hexane
  11. concentrationethyl acetate (=2:1) eluate was concentrated under reduced pressure, whereby the title compound (59 mg, 54%)
  12. customwas obtained as a white solid

Sources & evidence

ORD record
ord-df7f026213054092901148f167e8c2a2
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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