Potassium Carbonate → HCID 16118115, compound

HRID 1636035Notes

Reaction equation

HRID 1636035 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]=[N:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 500440126029-68-5

Product 1

HCID 16118115HCID 16118115, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.2 mol (44.6 g) of 4-hydroxy-4′-cyanoazobenzene, 2 mol (488.1 g) of 1,6-dibromohexane, 1.45 mol (220.4 g) of K2CO3 and 800 ml of acetone were charged in a 2-liter three-necked flask and reacted under reflux for 20 hours by using a water bath. After cooling to a room temperature, by-products and excess K2CO3 were removed by filtration. After concentrating to about 1/2 by using a rotary evaporator, the product was left in a refrigeration box to be crystallized. After filtration under suction, crystals were washed with n-hexane and dried under a reduced pressure (0.117 mol (45.3 g, yield; 58.6%)). Further, they were recrystallized in ethanol to obtain 0.094 mol of 4-(6-bromohexyloxy)-4′-cyanoazobenzene (36.3 g, yield: 47.0%)

Workup

  1. customreacted
  2. temperatureunder reflux for 20 hours
  3. customby-products and excess K2CO3 were removed by filtration
  4. concentrationAfter concentrating to about 1/2
  5. customa rotary evaporator
  6. waitthe product was left in a refrigeration box
  7. customto be crystallized
  8. filtrationAfter filtration under suction, crystals
  9. washwere washed with n-hexane
  10. customdried under a reduced pressure (0.117 mol (45.3 g, yield; 58.6%))
  11. customFurther, they were recrystallized in ethanol

Sources & evidence

ORD record
ord-80794a7c4135400b8c1d54e99052416e
Source dataset
uspto-grants-2003_01
Patent number
US06512085B1

Reaction notes

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