Chlorosulfonic acid → 4-(2-Methyl-1,3-oxazol-5-yl)benzenesulfonyl chloride

HRID 29520Notes

Reaction equation

HRID 29520 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:11][CH:12]=2)=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 2484912-Methyl-5-Phenyl-1,3-Oxazole

Product 1

HCID 529970604-(2-Methyl-1,3-oxazol-5-yl)benzenesulfonyl chloride

Procedure

2-Methyl-5-phenyl-oxazole (1.6 g, 10 mmol), prepared according to the literature procedure (Varma, R. S.; Kumar, D. J. Heterocyclic Chem., 1998, 35,1533), was dissolved in chlorosulfonic acid (10 mL) and stirred at room temperature for 16 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 0.82 g of the desired title compound as tan 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-5aaeba7832794bec81dd92221ad0615a
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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