Acetic Acid → 4-Bromo-2-methylbenzene-1-sulfonamide

HRID 380043Notes

Reaction equation

HRID 380043 reaction equation
[Br:1][C:2]1[CH:3]=C([CH:6]=[CH:7][C:8]=1C)N.N([O-])=O.[Na+].Cl.[Cl-].[Mg+2].[Cl-].[S:18](=[O:20])=[O:19].[OH-].[NH4+:22].[C:23](O)(=O)[CH3:24]>[Cu](Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([S:18]([NH2:22])(=[O:20])=[O:19])=[C:23]([CH3:24])[CH:3]=1

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 14923Ammonium HydroxideHCID 82187Benzenamine, 3-bromo-4-methyl-HCID 5360315Magnesium ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 206167674-Bromo-2-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

Prepared by the method of Example 69a) using 3-bromo-4-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 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 (1.51 g).

Workup

  1. customPrepared by the method of Example 69a)

Sources & evidence

ORD record
ord-6eed423eaf45419abf435b98bb927e2c
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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