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

HRID 252248Notes

Reaction equation

HRID 252248 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]>C(Cl)(Cl)Cl>[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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
4 °C

Procedure

To a chilled solution (ice-bath) of 4-methyl-5-phenyl-oxazole (0.2 g, 1.3 mmol) in CHCl3 (1 ml) was added drop-wise chlorosulfonic acid (0.5 ml, 7.7 mmol). The dark-brown reaction mixture was stirred at 4° C. for 30 min and slowly warmed to reflux. After 2 h the reaction mixture was poured into ice-water and extracted with ethyl acetate (3×). The combined organic extracts were washed with water, brine, dried (MgSO4.2H2O), filtered and evaporated to yield a light-brown solid: 0.19 g, (56%), MS: m/e 257.1.

Workup

  1. temperatureslowly warmed to reflux
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (MgSO4.2H2O)
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a light-brown solid

Sources & evidence

ORD record
ord-c652ab7c0f88496fa3853ee12ea694a5
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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