Hydrochloric Acid → 5-bromo-2-methylbenzenesulfonamide

HRID 380041Notes

Reaction equation

HRID 380041 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)N.N([O-])=O.[Na+].Cl.[Cl-].[Mg+2].[Cl-].[S:18](=[O:20])=[O:19].[OH-].[NH4+:22]>[Cu](Cl)Cl.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([S:18]([NH2:22])(=[O:20])=[O:19])[CH:8]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 14923Ammonium HydroxideHCID 27348055-Bromo-o-toluidineHCID 5360315Magnesium ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 24468215-bromo-2-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Prepared by the method of Example 69a) using 5-bromo-2-methylaniline (2.60 g, Example 78a)), sodium nitrite (1.05 g), concentrated hydrochloric acid (20 ml), anhydrous magnesium chloride (2.6 g), acetic acid saturated with sulfur dioxide (50 ml) and containing copper (II) chloride (0.37 g). The normal work-up and subsequent treatment with ammonium hydroxide (50 ml) followed by the same work-up afforded the subtitle compound as a solid (0.42 g).

Workup

  1. customPrepared by the method of Example 69a)

Sources & evidence

ORD record
ord-d12a56a04d1143e196f3be0f5add6546
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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