Chlorosulfonic acid → 4-(4-methyl-oxazol-5-yl)-benzenesulfonyl Chloride

HRID 29521Notes

Reaction equation

HRID 29521 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 594392Oxazole, 4-methyl-5-phenyl-

Product 1

HCID 597885434-(4-methyl-oxazol-5-yl)-benzenesulfonyl Chloride

Procedure

4-methyl-5-phenyl-oxazole (1.6 g, 10 mmol), prepared according to the literature (Heterocycles, 1977, 7, 77-80), was dissolved in chlorosulfonic acid (10 mL) and stirred at room temperature for 4 h. The reaction mixture was added to crushed ice (50 g) and the product was extracted with ether (3×50 mL). The combined organic extract was dried over anhydrous Na2SO4 and ether was evaporated. The product was purified by flash chromatography (silica-gel, 5-20% ethylacetate/hexane mobile phase) to yield 0.91 g of the desired-title compound light yellow solid. MS: m/z 258.0 (M++1).

Workup

  1. additionThe reaction mixture was added
  2. extractionthe product was extracted with ether (3×50 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over anhydrous Na2SO4 and ether
  5. customwas evaporated
  6. customThe product was purified by flash chromatography (silica-gel, 5-20% ethylacetate/hexane mobile phase)

Sources & evidence

ORD record
ord-f9885b2b86494950b21707d105682bc4
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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