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Ethylenediamine → 2-Amino-1,5-naphthalenedisulfonic acid

HRID 2210621
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2210621
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:7][C:8]=2O)[C:3]=1[S:17]([OH:20])(=[O:19])=[O:18].FC1N=NN=C(F)C=1F.C(N)CN.FC1N=NN=C(F)C=1>>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([S:13]([OH:16])(=[O:14])=[O:15])=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]=1[S:17]([OH:20])(=[O:19])=[O:18]
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Komponenten

5

Edukt 4

HCID 3301EthylenediamineHCID 810242-Amino-5-hydroxynaphthalene-1,7-disulphonic acidHCID 138991444,5,6-Trifluoro-1,2,3-triazineHCID 19878636Difluorotriazine

Produkt 1

HCID 83382-Amino-1,5-naphthalenedisulfonic acidAusbeute 100 %

Versuchsvorschrift

31.9 g of 2-amino-5-hydroxy-naphthalene-1,7-disulphonic acid are subjected to a condensation reaction with trifluorotriazine as described in Example 1. 5.0 g of ethylenediamine are added to the solution of the resulting difluorotriazine compound at 0°, a pH of 5.5-6.5 being maintained. The condensation has ended after 2 to 3 hours. A diazo compound obtained by the customary route by diazotisation of 30.3 g of 2-amino-naphthalene-1,5-disulphonic acid is added to the reaction product of the formula ##STR20## which is largely present as a suspension, the pH simultaneously being kept at pH 7.0-7.5 by sprinkling in sodium bicarbonate. When the coupling has ended, the dyestuff of the formula ##STR21## which has precipitated as a sparingly soluble product, is filtered off with suction and stirred in 1 l of water again. 16.9 g of 2,4,6-trifluoro-5-chloro-pyrimidine are added dropwise at 0°-5°, during which a pH of 7.5-8.0 is maintained with dilute sodium hydroxide solution. The dyestuff dissolves during the condensation reaction. When the condensation has ended (thin layer chromatogram), the dyestuff is salted out, filtered off with suction, dried and ground. The red powder dissolves readily in water and dyes cotton a clear scarlet (colour code number 6).

Aufarbeitung

  1. temperaturea pH of 5.5-6.5 being maintained

Quellen und Nachweise

ORD-Eintrag
ord-a2862839424f4443997a4deed569a808
Quelldatensatz
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05459246

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