N-bromobutanimide → HCID 18928115, Verbindung

HRID 1599411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599411
[Cl:1][C:2]1[C:3]2[N:4]([C:16]([CH3:24])=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=2.[Br:25]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:25][CH2:24][C:16]1[N:4]2[C:5]3[C:10]([N:11]=[C:2]([Cl:1])[C:3]2=[N:18][C:17]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:9][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:7][CH:6]=3

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 18928110HCID 18928110, Verbindung

Produkt 1

HCID 18928115HCID 18928115, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-2-ethoxycarbonyl-1-methyl-7-trifluoromethylimidazo[1,2-a]quinoxaline (830 g, 232 mmol), N-bromosuccinimide (68,0 g, 382 mmol) and 2,2'-azobis(2-methylpropionitrile)(200 mg, 1.2 mmol) in tetrachloromethane (1.5 l) was heated at reflux for 18 h, allowed to cool and the product collected by filtration. The product was dissolved in dichloromethane (2 l) and washed with water, dried (MgSO4), followed by purification with silica gel 60 (1 g). The organic phase was filtered and evaporated in vacuo. The residue was suspended in petroleum ether to yield 91.7 g (91%) of 1-bromomethyl-4-chloro-2-ethoxycarbonyl-7-trifluoromethyl-imidazo[1,2-a]quinoxaline which was collected by filtration. M.p. 196°-198° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. filtrationthe product collected by filtration
  5. dissolutionThe product was dissolved in dichloromethane (2 l)
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customfollowed by purification with silica gel 60 (1 g)
  9. filtrationThe organic phase was filtered
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fcf60b5290644ab5bc1db9f9532aa232
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741785

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