4-Amino-3-methylbenzenesulfonic acid → 4-Amino-3-methylbenzene-1-sulfonamide

HRID 890503

Reaction equation

HRID 890503 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](O)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[Cl-].ClC=[N+:16](C)C.C(Cl)(=O)C(Cl)=O.[OH-].[NH4+]>O1CCCC1.CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:16])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12]

Participants

7

Reactant 4

HCID 73844-Amino-3-methylbenzenesulfonic acidHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 77311Chloro-N,N-dimethylformiminium chloride

Product 1

HCID 1430374-Amino-3-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

For example, commercially available 2-aminotoluene-5-sulfonic acid was allowed to react with Villsmeyer reagent (N-(chloromethylene)-N-methylmethanaminium chloride), that is either commercially prepared or is generated in situ from a mixture of N,N-dimethylformamide and oxalyl chloride. The intermediate compound was then allowed to react with ammonium hydroxide in tetrahydrofuran to afford 4-amino-3-methylbenzenesulfonamide (Scheme IV).

Workup

  1. customeither commercially prepared

Sources & evidence

ORD record
ord-a0a0ea1488d74ce487d09f56374d3ea1
Source dataset
uspto-grants-2006_02
Patent number
US06995283B2

Linked notes

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