Diethyl Ether → Azobenzene

HRID 1013619Notes

Reaction equation

HRID 1013619 reaction equation
[C:1]1([N:7]=[N:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].C(OCC)C>O>[C:9]1([N:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1.[NH2:28][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([N:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 17974207HCID 17974207, compoundHCID 21226445Aluminium lithium hydride2×

Product 2

HCID 2272AzobenzeneHCID 17974206HCID 17974206, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A flask was charged with 1.008 g of the 11-[4-(phenylazo)phenyloxy]undecanamide, 0.624 g of aluminum lithium hydride, and 40 mL of dry diethylether, and the contents were put under reflux for 12 hours. The temperature was set back to a room temperature, and 20 mL of water was gradually dropped, so as to cause the excess aluminum lithium hydride to react with the water. Thereafter, the reaction solution was stirred for one day. Then, extraction from the reaction solution was performed three times by using 200 mL of diethylether, and the diethylether was removed by pressure-reduction. After that, a remaining supernatant was purified by recrystallization from a mixed solvent of chloroform and hexane. As a result, an intended amine derivative of 4-(phenylazo)benzene including a spacer group, i.e. 4-(11-aminoundecyloxy)azobenzene (azobenzene-O—(CH2)11NH2) was obtained at a 76% yield. A structure of the 4-(11-aminoundecyloxy)azobenzene was confirmed from a 1H-NMR spectrum and a 13C-NMR spectrum.

Workup

  1. temperatureunder reflux for 12 hours
  2. customwas set back to a room temperature
  3. extractionThen, extraction from the reaction solution
  4. customthe diethylether was removed by pressure-reduction
  5. customAfter that, a remaining supernatant was purified by recrystallization from a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-08ef447b9c334cce9adadc2d73835a9e
Source dataset
uspto-grants-2011_07
Patent number
US07981968B2

Reaction notes

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