Ethylenediamine → 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid

HRID 2395913Notes

Reaction equation

HRID 2395913 reaction equation
N1C(F)=NC(F)=NC=1F.N[C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14](C2C(C)=C(S(O)(=O)=O)C(C)=C(N)C=2C)=[CH:13][C:12]=1[S:41]([OH:44])(=[O:43])=[O:42].P([O-])([O-])(O)=O.[Na+].[Na+].[OH-].[Na+].C(N)CN>O>[CH:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[S:41]([OH:44])(=[O:43])=[O:42]

Participants

7

Reactant 5

HCID 3301EthylenediamineHCID 12664Cyanuric fluorideHCID 14798Sodium HydroxideHCID 24203Sodium Phosphate, DibasicHCID 21479582HCID 21479582, compound

Product 1

HCID 85529,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The compound can be prepared as follows: 14 parts of cyanuric fluoride are added dropwise to a neutral solution of 53 parts of 1-amino-4-(3-amino-2,4,6-trimethyl-5-sulfophenyl)anthraquinone-2-sulfonic acid and 5 parts of disodium hydrogenphosphate in 500 parts of water at a temperature below 2° C., while keeping the pH constant by the addition of sodium hydroxide solution. Upon completion of the reaction,a solution of 6 parts of ethylenediamine in 54 parts of water are added dropwise such that the temperature does not exceed 5 and the pH remains at6. The pH is then kept at 6. A solution of 1-amino-4-{3-[4-(2-amino-ethylamino)-6-fluoro-[1,3,5]-triazin-2-ylamino]-2,4,6-trimethyl-5-sulfophenyl)}-anthraquinone-2-sulfonic acid (solution 1) is obtained.

Workup

  1. customThe compound can be prepared

Sources & evidence

ORD record
ord-4db7f65c680047eea265db79773a34cd
Source dataset
uspto-grants-1996_02
Patent number
US05490866

Reaction notes

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