Phosphorus oxychloride → (1,2-Benzoxazol-3-yl)methanesulfonyl chloride

HRID 2223688Notes

Reaction equation

HRID 2223688 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][S:11]([OH:14])(=O)=[O:12])=[N:2]1.P(Cl)(Cl)([Cl:17])=O>>[CH:8]1[CH:9]=[C:4]2[C:3]([CH2:10][S:11]([Cl:17])(=[O:14])=[O:12])=[N:2][O:1][C:5]2=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 98777711,2-Benzisoxazole-3-methanesulfonic acid

Product 1

HCID 11390621(1,2-Benzoxazol-3-yl)methanesulfonyl chloride

Procedure

1,2-Benzisoxazole-3-methanesulfonic acid (1) (1.00 g, 4.7 mmol) was mixed with xylenes (10 mL) and phosphorous oxychloride (1.0 mL, 11 mmol) and heated to reflux until the reaction was complete. The mixture was filtered through CELITE™ and evaporated to dryness to yield 1,2-benzisoxazole-3-methanesulfonyl chloride (2) as a light brown solid. It was dissolved in ethyl acetate (10 mL), cooled in an ice-bath and treated with ammonia. Work-up analogous to example 2 gave pure zonisamide.

Workup

  1. temperatureheated
  2. temperatureto reflux until the reaction
  3. filtrationThe mixture was filtered through CELITE™
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-3a5159e2e98f4bbbba596e011308b714
Source dataset
uspto-grants-2008_05
Patent number
US07375233B2

Reaction notes

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