Chlorosulfonic acid → 2-Oxazol-5-YL-benzenesulfonyl chloride

HRID 29522Notes

Reaction equation

HRID 29522 reaction equation
[C:1]1([C:7]2[O:11][CH:10]=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[O:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[S:13]([Cl:12])(=[O:15])=[O:14])=[CH:8][N:9]=[CH:10]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 5893115-Phenyl oxazole

Product 1

HCID 552794732-Oxazol-5-YL-benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

5-Phenyloxazole (2.0 g, mmol) in chloroform (50 ml) was cooled to 0° C. using an ice bath. Chlorosulfonic acid 4.8 g (2.7 ml, 3 eq) of was added slowly with stirring. The reaction mixture was heated to 70° C. for 16 h. The reaction mixture was then cooled to RT, quenched with ice and extracted with chloroform. The organic layer was washed with cold water, brine and concentrated. The brown solid obtained was purified by column chromatography using 5% ethyl acetate in pet ether as eluent, to yield a yellow solid.

Workup

  1. temperatureThe reaction mixture was then cooled to RT
  2. customquenched with ice
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with cold water, brine
  5. concentrationconcentrated
  6. customThe brown solid obtained
  7. customwas purified by column chromatography
  8. customto yield a yellow solid

Sources & evidence

ORD record
ord-77ee1a4a12604140807a12e2e1e125b3
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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