Water → HCID 118869905, compound

HRID 1779125Notes

Reaction equation

HRID 1779125 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.C(O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]=[N:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)=[C:2]([O:1][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 136959807HCID 136959807, compound

Product 1

HCID 118869905HCID 118869905, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

10 g (37.3 mmol) of 4-((2-hydroxy-4-nitrophenyl)diazenyl)benzonitrile is dissolved in 200 mL of acetone, and 7.8 mL (44.9 mmol) of 1-bromooctane and 10.3 g (74.5 mmol) of potassium carbonate (K2CO3) are added thereto. Subsequently, the resultant reaction mixture is agitated at 60° C. for 24 hours while being refluxed, and then the temperature is lowered to room temperature. The reaction mixture is concentrated, dissolved in dichloromethane (CH2Cl2), passes through a silica gel pad, and the filtrated solution is recrystallized using dichloromethane (CH2Cl2) and n-hexane. The purified compound is dissolved in 150 mL of hot ethanol, and 12.5 g (74.4 mmol) of Na2S.5H2O dissolved in hot ethanol and water is added thereto. Subsequently the resultant reaction mixture is agitated at 80° C. for 5 hours, and then the temperature is lowered to room temperature. The resultant precipitated crystal is filtered, washed with water several times, and dried, thus obtaining 8.9 g (25.4 mmol) of 4-((4-amino-2-(octyloxy)phenyl)diazenyl)benzonitrile of the following Chemical Formula 1a-1. A yield is 68%.

Workup

  1. customSubsequently, the resultant reaction mixture
  2. temperaturewhile being refluxed
  3. customis lowered to room temperature
  4. concentrationThe reaction mixture is concentrated
  5. dissolutiondissolved in dichloromethane (CH2Cl2)
  6. customthe filtrated solution is recrystallized
  7. dissolutionThe purified compound is dissolved in 150 mL of hot ethanol
  8. customSubsequently the resultant reaction mixture
  9. stirringis agitated at 80° C. for 5 hours
  10. customis lowered to room temperature
  11. customThe resultant precipitated crystal
  12. filtrationis filtered
  13. washwashed with water several times
  14. customdried

Sources & evidence

ORD record
ord-adb88e86180240fdb69e13994e0cbf2b
Source dataset
uspto-grants-2016_02
Patent number
US09268065B1

Reaction notes

Loading…