4-Amino-3-methylbenzenesulfonic acid → Pyridinium 4-(acetylamino)-3-methylbenzenesulfonate

HRID 890504

Reaction equation

HRID 890504 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:9])=[O:10])=[CH:4][C:3]=1[CH3:12])(=[O:15])[CH3:14].[NH+:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 73844-Amino-3-methylbenzenesulfonic acidHCID 7918Acetic Anhydride

Product 1

HCID 22251061Pyridinium 4-(acetylamino)-3-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

For example, commercially available 2-aminotoluene-5-sulfonic acid was allowed to react with acetic anhydride in pyridine to afford pyridinium 4-(acetylamino)-3-methylbenzenesulfonate (Scheme V). The resulting salt was then allowed to react with sodium hydroxide to afford the corresponding sodium salt, sodium 4-(acetylamino)-3-methylbenzenesulfonate. The salt was then allowed to react with thionyl chloride to afford the intermediate sulfonyl chloride, followed by reaction with ammonia and subsequent deprotection by reaction with aqueous hydrochloric acid in ethanol to afford the desired sulfonamide.

Sources & evidence

ORD record
ord-5e2ea6ffbfc54c3993c8992b4a289042
Source dataset
uspto-grants-2006_02
Patent number
US06995283B2

Linked notes

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