Sodium Iodide → 2-Chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzene

HRID 65176

Reaktionsgleichung

Reaktionsgleichung von HRID 65176
[Cl:1][C:2]1[CH2:7][C:6]([N+:15]([O-:17])=[O:16])(C2C=CC(O)=CC=2)[CH:5]=[CH:4][C:3]=1[N:18]=[N:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:34](=[O:37])([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[N:18]=[N:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][C:34]([O:37][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 867410382-Chloro-4-nitro-4-(4-hydroxyphenyl)azobenzene

Produkt 1

HCID 202333592-Chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzeneAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.3 g of crude 2-chloro-4-nitro-4-(4-hydroxyphenyl)azobenzene, 20 ml of ethanol, 0.658 g of 1-bromoheptane, 0.528 g of potassium carbonate and a spatula tip of sodium iodide was boiled at reflux while stirring for 22 hours. The brown suspension was subsequently concentrated in vacuo and the residue was chromatographed on silica gel with toluene/hexane as the eluent. Recrystallization from methylene chloride/hexane, yielded 0.863 g of 2-chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzene as orange crystals; m.p. (C-N) 83.1°-83.7° C., cl.p. (N-I) 179.4°-179.8° C.; E300 =11580, E406 =25910.

Aufarbeitung

  1. temperatureat reflux
  2. concentrationThe brown suspension was subsequently concentrated in vacuo
  3. customthe residue was chromatographed on silica gel with toluene/hexane as the eluent
  4. customRecrystallization from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-7440c1c62ce147ae8b3c555fcbd6f3d9
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613208

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