Dimethylformamide → N-heptyl-3,6-Diformylcarbazole

HRID 1250803Notes

Reaction equation

HRID 1250803 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH2:11]([N:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:31]([O-])(=[O:33])C.[Na+]>O>[CH2:11]([N:18]1[C:30]2[CH:29]=[CH:28][C:27]([CH:31]=[O:33])=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[C:22]([CH:4]=[O:5])[CH:23]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychloride3×HCID 517045Sodium AcetateHCID 138604829-Heptyl-9H-carbazole

Product 1

HCID 11141782N-heptyl-3,6-DiformylcarbazoleYield 52.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1-liter, 3-neck round bottom flask equipped with mechanical stirrer, thermometer, and addition funnel, was added 271 ml DMF (3.5 mol). The contents were cooled in a salt/ice bath. When the temperature inside the flask reached 0° C., 326 ml of POCl3 (3.5 mol) was slowly added. During the addition of POCl3, the temperature inside the flask was not allowed to rise above 5° C. After the addition of POCl3 was completed, the reaction mixture was allowed to warm to room temperature. 126 g of N-heptylcarbazole was then added and the flask was heated to 90° C. for 24 hr. using a heating mantle. The reaction mixture was cooled to room temperature and the solution was added slowly to a 4.5 liter beaker containing a solution of 820 g sodium acetate dissolved in 2 liters of water. The beaker was cooled in an ice bath and stirred for 3 hr. The brownish solid obtained was filtered and washed repeatedly with water, followed by a small amount of ethanol (50 ml). The resulting product was recrystallized once from toluene using activated charcoal and dried under vacuum in an oven heated at 70° C. for 6 hr to obtain 80 g (51% yield) of N-heptyl-3,6-diformyl-carbazole. 1H-NMR and IR spectra confirmed the presence of N-heptyl-3,6-diformyl-carbazole.

Workup

  1. customTo a 1-liter, 3-neck round bottom flask equipped with mechanical stirrer
  2. additionthermometer, and addition funnel
  3. temperatureThe contents were cooled in a salt/ice bath
  4. customreached 0° C.
  5. customto rise above 5° C
  6. temperaturethe flask was heated to 90° C. for 24 hr
  7. temperatureThe reaction mixture was cooled to room temperature
  8. additionthe solution was added slowly to a 4.5 liter beaker
  9. temperatureThe beaker was cooled in an ice bath
  10. customThe brownish solid obtained
  11. filtrationwas filtered
  12. washwashed repeatedly with water
  13. customThe resulting product was recrystallized once from toluene using activated charcoal
  14. customdried under vacuum in an oven
  15. temperatureheated at 70° C. for 6 hr

Sources & evidence

ORD record
ord-e3d24d8308c645b19c072947b7c2cf95
Source dataset
uspto-grants-2002_01
Patent number
US06340548B1

Reaction notes

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