Cyanuric chloride → 2-Amino-5-methylbenzenesulfonic acid

HRID 2164710

Reaction equation

HRID 2164710 reaction equation
N1C(Cl)=NC(Cl)=N[C:2]=1Cl.[Na].[NH2:11][C:12]1[CH:17]=[C:16](N)[CH:15]=[CH:14][C:13]=1[S:19]([OH:22])(=[O:21])=[O:20]>>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:2])=[CH:14][C:13]=1[S:19]([OH:22])(=[O:21])=[O:20]

Participants

4

Reactant 3

HCID 7954Cyanuric chlorideHCID 666232,4-Diaminobenzenesulfonic acidHCID 5360545Sodium

Product 1

HCID 69342-Amino-5-methylbenzenesulfonic acid

Procedure

31.4 Parts of 8-amino-naphthol-3,6-disulphonic acid are condensed with cyanuric chloride at 0° C. and pH 1 to 2. To the suspension of the primary condensation product is added an aqueous solution of 21 parts of the sodium salt of 2,4-diaminobenzenesulphonic acid and condensation is effected at a pH of 4 to 5. When the condensation is complete, the secondary condensation product is coupled at pH 6 to 6.5 with the diazo compound obtained from 18.7 parts of 2-amino-5-methylbenzenesulphonic acid. The red dye solution is then added to a suspension of 2-(2'-sulphophenylamino)-4,6-difluoro-1,3,5-triazine prepared by condensing 17.3 parts of 2-aminobenzenesulphonic acid with 13.5 parts of 2,4,6-trifluoro-1,3,5-triazine at 0° C. The hydrogen fluoride liberated during the condensation is neutralised continously by adding sodium carbonate solution. When the condensation is complete, the reaction product is isolated in the form of a red powder by evaporating the water under reduced pressure. The dye colours cellulose fibres in fast, bluish red shades.

Workup

  1. additionTo the suspension of the primary condensation product
  2. additionis added

Sources & evidence

ORD record
ord-373bb48eedf64b16820f13e76ae84249
Source dataset
uspto-grants-1985_03
Patent number
US04507236

Linked notes

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