Chloroacetyl chloride → 1,8-Bis(chloroacetamido)anthraquinone

HRID 556198

Reaktionsgleichung

Reaktionsgleichung von HRID 556198
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH2:17])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>CN(C=O)C.N1C=CC=CC=1>[Cl:19][CH2:20][C:21]([NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH:17][C:21](=[O:22])[CH2:20][Cl:19])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:22]

Komponenten

5

Edukt 2

HCID 6577Chloroacetyl chlorideHCID 85111,8-Diamino-9,10-anthracenedione

Produkt 1

HCID 469280411,8-Bis(chloroacetamido)anthraquinoneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 1,8-diaminoanthraquinone (0.476 g, 2.0 mmol) in 20 ml DMF. Add pyridine (0.5 ml) as catalyst in an ice bath. Then add chloroacetyl chloride (0.5 ml, 6 mmol) into the solution, remove the ice bath, introduce nitrogen, protect from light, and stir the solution at room temperature for 24 hours. The reacted solution is poured into ice water (50 ml), filtered to get precipitate. At last, the precipitate is recrystallized to get yellow compound 3.

Aufarbeitung

  1. additionintroduce nitrogen
  2. filtrationfiltered
  3. customto get precipitate
  4. customAt last, the precipitate is recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-9df7afb5faf0465792353d68acb00dbb
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053583B2

Verknüpfte Notizen

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