Chlorosulfonic acid → 4-(1-Methyl-1-oxazol-4-yl-ethyl)-benzenesulfonyl Chloride

HRID 29516Notes

Reaction equation

HRID 29516 reaction equation
[CH3:1][C:2]([C:10]1[N:11]=[CH:12][O:13][CH:14]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[Cl:15][S:16](O)(=[O:18])=[O:17]>C(Cl)(Cl)Cl>[CH3:3][C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:6][CH:5]=1)([C:10]1[N:11]=[CH:12][O:13][CH:14]=1)[CH3:1]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acid2×HCID 597885594-(1-Methyl-1-phenyl-ethyl)-oxazole

Product 1

HCID 597887344-(1-Methyl-1-oxazol-4-yl-ethyl)-benzenesulfonyl Chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 261 mg (1.4 mmol) of 4-(1-Methyl-1-phenyl-ethyl)-oxazole in 15 ml of chloroform at 0° C. was added 0.49 gm (4.2 mmol) of chlorosulfonic acid. After 30 minutes, the solution was allowed to warm to ambient temperature and an additional 0.49 gm (4.2 mmol) of chlorosulfonic acid was added. After one hour, the mixture was cooled in an ice/water bath, and crushed ice was added to the reaction. The mixture was partitioned between 1M pH=7 phosphate buffer and ether, and the phases were separated. The ether phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude title product as an oil.

Workup

  1. waitAfter one hour
  2. temperaturethe mixture was cooled in an ice/water bath
  3. customcrushed ice
  4. additionwas added to the reaction
  5. customThe mixture was partitioned between 1M pH=7 phosphate buffer and ether
  6. customthe phases were separated
  7. washThe ether phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ccf33f9671d4217853eca7aeedd625b
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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