Water → 2-Aminobenzenesulfonic acid

HRID 2418664Notes

Reaction equation

HRID 2418664 reaction equation
[NH2:1]C1C2C(=CC(S(O)(=O)=O)=CC=2O)C=C(S(O)(=O)=O)C=1.C([O-])(=O)C.[Na+].ClCC[S:29]([C:32]1[CH:40]=[CH:39][C:35](C(Cl)=O)=[C:34](C)[CH:33]=1)(=[O:31])=[O:30].[OH2:42]>>[S:29]([C:32]1[CH:40]=[CH:39][CH:35]=[CH:34][C:33]=1[NH2:1])([OH:31])(=[O:30])=[O:42]

Participants

5

Reactant 4

HCID 962WaterHCID 7009H acidHCID 517045Sodium AcetateHCID 86739660HCID 86739660, compound

Product 1

HCID 69262-Aminobenzenesulfonic acid

Procedure

A neutral solution of 31.9 parts of 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid in 300 parts of water is prepared, 30 parts of crystalline sodium acetate are added and the mixture is cooled to 5° to 10° C. 31 parts of finely ground 4-(β-chloroethylsulfonyl)-methyl-benzoyl chloride are added in the course of 1 to 2 hours, with stirring, and stirring is then continued for several hours. A diazonium salt solution obtained from 14.1 parts of 2-sulfo-aniline are then allowed to run in, and the coupling reaction is carried out at a pH value of 6 to 7. The coupling solution is then clarified and the azo compound prepared is isolated from the filtrate in the customary manner, for example by evaporation, spray-drying or salting out.

Workup

  1. temperaturethe mixture is cooled to 5° to 10° C
  2. stirringstirring
  3. waitis then continued for several hours

Sources & evidence

ORD record
ord-c236cb393577455aa3bafe6d1770f61b
Source dataset
uspto-grants-1984_09
Patent number
US04473498

Reaction notes

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