Phosphorus oxychloride → (1,2-Benzoxazol-3-yl)methanesulfonyl chloride
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe mixture was heated
- temperatureto reflux until the reaction
- filtrationfiltered through CELITE™
- customevaporated
Sources & evidence
- ORD record
- ord-d84ee85de4e3468c8ff03664d9a3af6c
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375233B2
Reaction notes
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