Sodium Iodide → 81530-89-4

HRID 1075132Notes

Reaction equation

HRID 1075132 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[I-].[Na+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 150354-[(4-Nitrophenyl)azo]phenol

Product 1

HCID 2049416981530-89-4

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.1 g of 4-nitro-4'-hydroxy-azobenzene, 15 mg of sodium iodide, 2.27 g of 1-bromo-heptane, 1.8 g of potassium carbonate and 20 ml of ethanol is heated under reflux for 60 hours. The solvent is removed in vacuo, water is added and the mixture is exhaustively extracted with methylene chloride. The residue of 4.0 g (brown crystals) of 4-nitro-4'-heptyloxy-azobenzene, which remains after drying with sodium sulfate and removing the solvent by evaporation, is chromatographed on a column of 200 g of silica gel with methylene chloride. By recrystallization of the uniform fractions from acetone/hexane there is obtained the pure compound as orange crystals; m.p. 82.3°-83.2° C., liquid crystalline, conversion at 93.7° C., cl.p. 96.4° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 60 hours
  3. customThe solvent is removed in vacuo, water
  4. additionis added
  5. extractionthe mixture is exhaustively extracted with methylene chloride
  6. dry with materialafter drying with sodium sulfate
  7. customremoving the solvent
  8. customby evaporation
  9. customis chromatographed on a column of 200 g of silica gel with methylene chloride
  10. customBy recrystallization of the uniform fractions from acetone/hexane there

Sources & evidence

ORD record
ord-0714aeec7a8744dd89cc43fa3831fcc7
Source dataset
uspto-grants-1983_07
Patent number
US04395350

Reaction notes

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