Potassium Carbonate → HCID 22616834, compound

HRID 843217Notes

Reaction equation

HRID 843217 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+].[Cl-].[Cl-].[Ca+2]>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:13][CH:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 500440126029-68-5HCID 5284359Calcium Chloride

Product 1

HCID 22616834HCID 22616834, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

15.06 g (0.067 mol) of 4-(4-cyanophenylazo)phenol, 14.99 g (0.067 mol) of ethyl 6-bromo-hexanoate (Aldrich, 99%) and 11.76 g (0.085 mol) of oven dried K2CO3 were mixed in a 250 mL one-neck round flask fitted with a magnetic stirring bar. 160 mL of dry acetone was added, the flask was closed with a reflux condenser protected on the top with a CaCl2-drying tube and the stirred solution was refluxed on an oil bath at 60° C. for 72 h. After cooling the flask was transferred to a Rotavapor and the acetone was removed by rotary evaporation. The resulting solid mixture was added 200 mL of hot water and stirred. The aqueous mixture was allowed to cool and then filtered by suction from a water aspirator. The undried filtercake was transferred to a 500 mL Erlenmeyer flask, 300 mL of ethanol was added and the content of the flask brought to boiling. After cooling 20.46 g (yield 83%) of ethyl 6-[4-(4-cyanophenyl-azo)phenoxy]-hexanoate was filtered off. The crude ethyl 6-[4-(4cyanophenylazo)phenoxy]-hexanoate was recrystallized from 750 mL of ethanol and then repeatedly from 650 mL of ethanoL After vacuum drying at 50° C. for 20 h a final yield of 17.21 g (70%) was obtained.

Workup

  1. customfitted with a magnetic stirring bar
  2. customthe flask was closed with a reflux condenser
  3. customdrying tube
  4. temperatureAfter cooling the flask
  5. customthe acetone was removed by rotary evaporation
  6. additionThe resulting solid mixture was added 200 mL of hot water
  7. temperatureto cool
  8. filtrationfiltered by suction from a water aspirator
  9. additionwas added

Sources & evidence

ORD record
ord-1cd0ea2ec8904d8281f8c871d4badfc8
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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