Dimethylformamide → 7-Bromo-2-chloroquinoxaline

HRID 927313

Reaktionsgleichung

Reaktionsgleichung von HRID 927313
S(Cl)([Cl:3])=O.CN(C)C=O.[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([N:15]=[CH:16][C:17](=O)[NH:18]2)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([N:15]=[CH:16][C:17]([Cl:3])=[N:18]2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 49132647-bromo-1H-quinoxalin-2-one

Produkt 1

HCID 49132537-Bromo-2-chloroquinoxalineAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Thionyl chloride (407.5 mL; 5.59 mol), then N,N-dimethylformamide (34.6 mL; 0.45 mol) were added dropwise to a mixture of 7-bromo-2(1H)-quinoxalinone (500 g; 2.24 mol) in toluene (7.61 L). The reaction mixture was stirred at 80° C. for 17 hours then cooled to 35° C. and poured cautiously onto water. The bi-phasic mixture was stirred for 30 minutes and then decanted. The organic layer was evaporated to dryness and the residue crystallized in methyl-tert-butyl ether, filtered and the precipitate washed with methyl-tert-butyl ether and dried to give 407 g (74.7%) of 7-bromo-2-chloro-quinoxaline. Filtrate was evaporated and re-crystallized in methyl-tert-butyl ether to provide a second fraction of 72 g (13.2%) of 7-bromo-2-chloro-quinoxaline.

Aufarbeitung

  1. temperaturethen cooled to 35° C.
  2. additionpoured cautiously onto water
  3. stirringThe bi-phasic mixture was stirred for 30 minutes
  4. customdecanted
  5. customThe organic layer was evaporated to dryness
  6. customthe residue crystallized in methyl-tert-butyl ether
  7. filtrationfiltered
  8. washthe precipitate washed with methyl-tert-butyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bcf8466d5cd1409b82b935532da66576
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290478B2

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