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

HRID 2223689Notes

Reaction equation

HRID 2223689 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>ClCCCl>[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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1,2-Benzisoxazole-3-methanesulfonic acid (1) (1.00 g, 4.7 mmol) was mixed with 1,2-dichloroethane (10 mL) and phosphorous oxychloride (2.0 mL, 21 mmol). The mixture was heated to reflux until the reaction was complete, filtered through CELITE™ and evaporated to give 1,2-benzisoxazole-3-methanesulfonyl chloride (2). It was converted into zonisamide in analogy to the previous examples.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux until the reaction
  3. filtrationfiltered through CELITE™
  4. customevaporated

Sources & evidence

ORD record
ord-d84ee85de4e3468c8ff03664d9a3af6c
Source dataset
uspto-grants-2008_05
Patent number
US07375233B2

Reaction notes

Loading…