Thionyl Chloride → HCID 23028558, compound

HRID 748727Notes

Reaction equation

HRID 748727 reaction equation
S(Cl)(Cl)=O.[O:5]1[C:9]([CH2:10]O)=[CH:8][N:7]=[CH:6]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[Na+].C([O-])(=O)C.[K+]>C(O)CCC.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:10][C:9]2[O:5][CH:6]=[N:7][CH:8]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 517044Potassium AcetateHCID 187589851,3-Oxazol-5-ylmethanolHCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 23028558HCID 23028558, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (188 μl, 2.57 mmol) was added to a chloroform (10 ml) solution of oxazol-5-ylmethanol (85 mg, 0.858 mmol). The resulting mixture was stirred at 50° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was dissolved in butanol (10 ml). To the resulting solution were added sodium 4-chlorobenzenesulfinate (170 mg, 0.858 mmol), potassium acetate (252 mg, 2.57 mmol) and tetrabutylammonium iodide (15 mg), followed by stirring at 70° C. for 3 days. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue. The mixture was washed successively with water 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, and the fraction obtained from the hexane:ethyl acetate (=1:1) fraction was concentrated under reduced pressure, whereby the title compound (81 mg, 37%) was obtained as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. stirringby stirring at 70° C. for 3 days
  5. temperatureAfter cooling to room temperature
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. washThe mixture was washed successively with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customthe fraction obtained from the hexane
  13. concentrationethyl acetate (=1:1) fraction was concentrated under reduced pressure, whereby the title compound (81 mg, 37%)
  14. customwas obtained as a white solid

Sources & evidence

ORD record
ord-47d62874aa934ed8aad86fc5845af637
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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