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

HRID 65176

Reaction equation

HRID 65176 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 202333592-Chloro-4-nitro-4'-(4-heptyloxyphenyl)-azobenzeneYield 104.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7440c1c62ce147ae8b3c555fcbd6f3d9
Source dataset
uspto-grants-1986_09
Patent number
US04613208

Linked notes

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