2(3H)-Benzoxazolone → 6-Benzoxazolesulfonyl chloride, 2,3-dihydro-2-oxo-

HRID 243619

Reaction equation

HRID 243619 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:10][C:8](=[O:9])[NH:7][C:5]=2[CH:6]=1.[Cl:11][S:12](O)(=[O:14])=[O:13]>>[O:9]=[C:8]1[NH:7][C:5]2[CH:6]=[CH:1][C:2]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:3][C:4]=2[O:10]1

Participants

3

Reactant 2

HCID 60432(3H)-BenzoxazoloneHCID 24638Chlorosulfonic acid

Product 1

HCID 1196986-Benzoxazolesulfonyl chloride, 2,3-dihydro-2-oxo-Yield 73%

Conditions

Temperature
25 °C

Procedure

Benzoxazolinone (13.5 g, 0.1 mol) was added slowly to a 0° C. solution of chlorosulfonic acid (33.29 mL, 5 equivalents). The reaction was warmed to 25° C. and stirred for 0.5 h, heated to 60° C. for 3 h. The reaction was cooled to 25° C., poured into ice, filtered, and rinsed with water. The resulting white solid was redissolved in 500 mL of diethyl ether and washed with water (2×), dried over Na2SO4, filtered and concentrated to 100 mL volume. Hexane was added (100 mL) and the white precipitate was filtered and placed under vacuum to yield 17 g (73%) of the title compound.

Workup

  1. temperatureheated to 60° C. for 3 h
  2. temperatureThe reaction was cooled to 25° C.
  3. additionpoured into ice
  4. filtrationfiltered
  5. washrinsed with water
  6. dissolutionThe resulting white solid was redissolved in 500 mL of diethyl ether
  7. washwashed with water (2×)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to 100 mL volume
  11. additionHexane was added (100 mL)
  12. filtrationthe white precipitate was filtered

Sources & evidence

ORD record
ord-2e0e71705f134b14b14c40d3045550a3
Source dataset
uspto-grants-2014_02
Patent number
US08653141B2

Linked notes

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