Methanesulfonyl chloride → HCID 86730300, compound

HRID 1053967Notes

Reaction equation

HRID 1053967 reaction equation
[OH:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[C:7]#[N:8].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>C(Cl)Cl.O>[CH3:9][S:10]([O:1][CH:2]1[CH:3]([C:7]#[N:8])[CH2:4][S:5][CH2:6]1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86730301HCID 86730301, compound

Product 1

HCID 86730300HCID 86730300, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-hydroxytetrahydrothiophene-3-carbonitrile (1.0 g, 7.7 mmol) in DCM (15 mL) was stirred at 0° C. TEA (4.3 mL, 31 mmol) was added followed by the dropwise addition of methanesulfonyl chloride (1.77 g, 15.5 mmol). The resulting mixture was stirred at 0° C. for 30 minutes then warmed to ambient temperature and stirred for an additional 30 minutes. The mixture was carefully diluted with water and extracted with DCM (2×). The combined organic extracts were washed with 1N aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (using a gradient elution of 0-5% MeOH/DCM) to afford the title compound, which was used without further purification.

Workup

  1. temperaturethen warmed to ambient temperature
  2. stirringstirred for an additional 30 minutes
  3. extractionextracted with DCM (2×)
  4. washThe combined organic extracts were washed with 1N aqueous HCl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by MPLC on silica gel (
  9. washa gradient elution of 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-6b6f60c240584a4fa845607064e75263
Source dataset
uspto-grants-2016_07
Patent number
US09394282B2

Reaction notes

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