1,2-Dibromoethane → HCID 838311, Verbindung

HRID 127906

Reaktionsgleichung

Reaktionsgleichung von HRID 127906
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[Br:16][CH2:17][CH2:18]Br.[OH-].[Na+].C1(=O)C2C(C3C(N=2)=CC=CC=3)=CC=C1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][CH2:17][Br:16])[C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1

Komponenten

7

Edukt 4

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 6079846-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-oneHCID 22065876Carbazolone

Produkt 1

HCID 838311HCID 838311, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

199 g. (1 mole) of 6-methyl-1,2,3,4-tetrahydrocarbazol-1-one (m.p.: 199° C., as given in literature: 194°-195° C., 195°-196° C., 195° C., cf. Bloink and Pausacker loc. cit. page 1330), 1520 g. (8.1 moles), 1,2-dibromoethane and 1000 ml. (7.5 moles) of aqueous sodium hydroxide solution (30% strength) are taken initially and admixed, while stirring at room temperature, with 4.25 g. (12.5 m mole) of tetrabutylammoniumhydrogensulfate dissolved in 25 ml of water. With a slight temperature rise, the reaction sets in and while continuously stirring, comes to an end after some seven hours' time. For working up, the aqueous alkaline layer is separated, the organic layer washed with water and the excess dibromoethane distilled off in vacuo. The residue is recrystallized from 200 ml. of ethanol. 281 g. (92% of the theoretical) of 6-methyl-9-(2-ethylbromide)-1,2,3,4-tetrahydrocarbazol-1-one (melting at 103° C.). The amount of the tetrabutylammoniumhydrogensulfate used as catalyst can be reduced to 5 m moles per 1 mole of the carbazolone employed, but the reaction takes twice as long when this change is made.

Aufarbeitung

  1. stirringwhile continuously stirring
  2. customthe aqueous alkaline layer is separated
  3. washthe organic layer washed with water
  4. distillationthe excess dibromoethane distilled off in vacuo
  5. customThe residue is recrystallized from 200 ml

Quellen und Nachweise

ORD-Eintrag
ord-33562c8b56c04b2192f44077a9edea37
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04258043

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