1,3-Dibromo-5,5-dimethylhydantoin → 2-(1-Bromoethyl)-3,5-dichloroquinoxaline

HRID 1019809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019809
[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([Cl:12])[CH:8]=[CH:7][CH:6]=2.[Br:15]N1C(C)(C)C(=O)N(Br)C1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:13]([C:3]1[C:2]([Cl:1])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:12])[N:4]=1)[CH3:14]

Komponenten

5

Edukt 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 866985103,5-Dichloro-2-ethylquinoxaline

Produkt 1

HCID 866985112-(1-Bromoethyl)-3,5-dichloroquinoxalineAusbeute 129 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3,5-Dichloro-2-ethylquinoxaline (1.10 Kg, 4.84 mol) was dissolved in CCl4 (4.4 L) at rt. 1,3-dibromo-5,5-dimethylhydantoin (762 g, 2.66 mol) and benzoyl peroxide (116 g, 0.48 mol) were then added. The resulting suspension was heated at reflux for 2 h. At this time LC-MS analysis showed that the reaction was complete. After cooling to rt white crystals formed in the reaction vessel. The white crystals were collected by filtration, washed with saturated aqueous NaHCO3 (3×5 L), and dried under high vacuum to give 2-(1-bromoethyl)-3,5-dichloroquinoxaline as a white solid (1.05 Kg). 1H NMR (DMSO-d6) δ ppm 8.04-8.12 (m, 2H), 7.78-7.90 (m, 1H), 5.76-5.84 (m, 1H), 2.09 (d, J=6.7 Hz, 3H). Mass Spectrum (ESI) m/z=304.8 [(M+1) (79Br)], 306.9 [(M+1) (81Br)].

Aufarbeitung

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 h
  3. customformed in the reaction vessel
  4. filtrationThe white crystals were collected by filtration
  5. washwashed with saturated aqueous NaHCO3 (3×5 L)
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bddd886454ef4a29a3aa054e356d2cbd
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716290B2

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