Chlorosulfonic acid → 4-(1-Methyl-1-oxazol-5-yl-ethyl)benzenesulfonyl Chloride

HRID 29519Notes

Reaction equation

HRID 29519 reaction equation
[CH3:1][C:2]([C:10]1[O:14][CH:13]=[N:12][CH:11]=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]>>[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[O:14][CH:13]=[N:12][CH:11]=1)[CH3:1]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 597887885-(1-Methyl-1-phenylethyl)oxazole

Product 1

HCID 597886214-(1-Methyl-1-oxazol-5-yl-ethyl)benzenesulfonyl ChlorideYield 63%

Conditions

Temperature
60 °C

Procedure

A solution of 5-(1-Methyl-1-phenylethyl)oxazole (3.87 mmol, 1.0 eq.) in CDCl3 (0.3 mL) was stirred at 0° C. and chlorosulfonic acid (11.7 mmol, 3.0 eq.)was slowly added in. The mixture was heated to 60° C. for 3 h and cooled to room temperature. The solution was further mixed with crushed ice (15 g) and extracted with EtOAc (3×15 mL). The extracts were combined, washed by saturated aqueous NaCl solution, dried by MgSO4, filtered and concentrated in vacuo to afford the title compound as a pale yellow oil (697 mg, 63%) which was used as it was. 1H NMR: δ (400 MHz, CDCl3) 7.97 (d, 2H), 7.83 (s, 1H), 7.47 (d, 2H), 6.96 (s, 1H), 1.74 (s, 6H). MS (M+H+): 286.0

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (3×15 mL)
  3. washwashed by saturated aqueous NaCl solution
  4. dry with materialdried by MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e427a3cc40cb4415a0417a3eb0a042c4
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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