Sodium Sulfite → 1,2-Benzisoxazole-3-methanesulfonate sodium

HRID 1591957Notes

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4]2[O:9][N:8]=[C:7]([CH2:10][S:11]([OH:14])(=[O:13])=N)[C:5]=2[CH:6]=1.BrCC1C2C=CC=CC=2[O:19]N=1.S([O-])([O-])=O.[Na+:30].[Na+]>>[Na+:30].[O:9]1[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[C:7]([CH2:10][S:11]([O-:14])(=[O:19])=[O:13])=[N:8]1

Participants

Reactant 3

HCID 24437Sodium Sulfite

HCID 34991891,2-Benzisoxazole, 3-(bromomethyl)-

HCID 119678001,2-Benzoxazol-3-ylmethanesulfonimidic acid

Product 1

HCID 236749341,2-Benzisoxazole-3-methanesulfonate sodium

Procedure

A process for the preparation of zonisamide, disclosed in U.S. Pat. No. 4,172,896, comprises the sulfonation of 3-bromomethyl-benzo[d]isoxazole (1) with sodium sulfite to obtain benzo[d]isoxazol-3-yl-methanesulfonic acid sodium salt (2) which is then transformed into the corresponding sulfonyl chloride (3) by treatment with phosphorous oxychloride. The reaction of the latter with gas ammonia yields zonisamide (4), as reported hereinbelow.

Sources & evidence

ORD record: ord-92c25a434cfe454498b138c684825bd0
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291742B2

Reaction notes

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