Hydrogen Bromide → Sodium

HRID 1175057Notes

Reaction equation

HRID 1175057 reaction equation
N[C:2]1[C:7]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][C:3]=1[S:16]([OH:19])(=[O:18])=[O:17].[Na:20].[BrH:21].N([O-])=O.[Na+]>O>[Br:21][C:2]1[C:7]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][C:3]=1[S:16]([OH:19])(=[O:18])=[O:17].[Na:20]

Participants

7

Reactant 4

HCID 260Hydrogen Bromide2×HCID 5360545SodiumHCID 140094052-Aminobenzene-1,3,5-trisulfonic acidHCID 23668193Sodium Nitrite

Product 2

HCID 5360545SodiumHCID 19778783HCID 19778783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The 2-amino-benzene-1,3,5-trisulfonic acid, sodium salt can be dissolved in water and treated with 48% hydrobromic acid (5 equivalents). A solution of sodium nitrite (2 equivalents) in water can be added dropwise and stirred until the precipitation of the diazonium salt is complete. A solution of cuprous bromide (1 equivalent) in 48% hydrobromic acid (5 equivalents) can be added in one portion and the mixture stirred until gas evolution ceases followed by heating to a reflux. The solution can be evaporated and the residue dissolved in water followed by neutralization to pH 7 using sodium bicarbonate. The solids can be filtered off, the filtrate evaporated, and the solids dried under vacuum. The product can be recrystallized from water by addition of ethanol to give 2-bromo-benzene-1,3,5-trisulfonic acid, sodium salt.

Workup

  1. temperatureby heating to a reflux
  2. customThe solution can be evaporated
  3. dissolutionthe residue dissolved in water
  4. filtrationThe solids can be filtered off
  5. customthe filtrate evaporated
  6. customthe solids dried under vacuum
  7. customThe product can be recrystallized from water by addition of ethanol

Sources & evidence

ORD record
ord-1ba1b6ce3a6341fbb2cd852070124740
Source dataset
uspto-grants-2010_11
Patent number
US07838594B2

Reaction notes

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