Thionyl Chloride → 2-(4-Chlorophenylsulfonylmethyl)thiazole

HRID 748726Notes

Reaction equation

HRID 748726 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6]O.S(Cl)(Cl)=O.[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(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 517044Potassium AcetateHCID 27952131,3-Thiazol-2-ylmethanolHCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 230287302-(4-Chlorophenylsulfonylmethyl)thiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a chloroform (15 ml) solution of thiazole-2-methanol (171 mg, 1.49 mmol) was added thionyl chloride (0.33 ml, 4.47 mmol) and the resulting mixture was stirred at 50° C. for 11 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in butanol (10 ml). To the resulting solution were added sodium 4-chlorobenzenesulfinate (296 mg, 1.49 mmol) and potassium acetate (292 mg, 2.98 mmol). The mixture was stirred at 70° C. for 24 hours. 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 chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (169 mg, 41%) was obtained as a pale yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in butanol (10 ml)
  4. stirringThe mixture was stirred at 70° C. for 24 hours
  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) eluate was concentrated under reduced pressure, whereby the title compound (169 mg, 41%)
  14. customwas obtained as a pale yellow solid

Sources & evidence

ORD record
ord-6ababcf648274069bd2d366565996408
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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