Epibromohydrin → 1,4-Bis(3-bromo-2-hydroxypropylamino)-9,10-anthracenedione

HRID 1110434

Reaktionsgleichung

[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH2:18])=[CH:4][CH:3]=1.[CH2:19]([CH:21]1[O:23][CH2:22]1)[Br:20]>C(O)(=O)C.O>[Br:20][CH2:19][CH:21]([OH:23])[CH2:22][NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH:18][CH2:22][CH:21]([OH:23])[CH2:19][Br:20])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

1,4-Diaminoanthraquinone (2,5 g, 10.49 mmole) was slurried in 20 ml of glacial acetic acid. Water (1.8 ml) was added, followed by epibromohydrin (0.76 ml, 8.88 mmol). The mixture was heated to 80° C. The remaining epibromohydrin (2.24 ml, 26.18 mmol) was dripped in slowly during 5 hours, while the reaction temperature was held at 80° C. After the addition was complete, the 80° C. temperature was maintained for an additional 2 hours for a total of 7 hours. The reaction mixture was diluted with 20 ml of acetic acid and 28 ml of water. After stirring for a few minutes, the resultant mixture was filtered and the filter-cake was rinsed with 20% aqueous acetic acid followed by water, then air dried. After further drying in vacuo over P2O5, 4.76 g of 1,4-bis(3-bromo-2-hydroxypropylamino)-9,10-anthracenedione was obtained.

Aufarbeitung

customslowly during 5 hours
customwas held at 80° C
additionAfter the addition
temperaturethe 80° C. temperature was maintained for an additional 2 hours for a total of 7 hours
filtrationthe resultant mixture was filtered
washthe filter-cake was rinsed with 20% aqueous acetic acid
customair dried
dry with materialAfter further drying in vacuo over P2O5

Quellen und Nachweise

ORD-Eintrag: ord-b75fe052d6cd453da53d7b1efc6bc3ca
Quelldatensatz: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04975459

Verknüpfte Notizen

Wird geladen…