Dimethylformamide → N-propylphenyl-3-formylcarbazole

HRID 1250804Notes

Reaction equation

HRID 1250804 reaction equation
[CH2:1]([N:4]1[C:16]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][CH3:3].CN([CH:26]=[O:27])C.O=P(Cl)(Cl)Cl>O>[CH2:1]([N:4]1[C:16]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:13]([CH:26]=[O:27])=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychloride3×HCID 69731188N-Propylphenylcarbazole

Product 1

HCID 86757732N-propylphenyl-3-formylcarbazoleYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 ml, three neck round bottom flask equipped with mechanical stirrer, thermometer, and addition funnel were added N-propylphenylcarbazole (56g, 0.2 mol) (prepared as described in the procedure used to prepare Compound (6)) and DMF (300 ml). The flask was placed in an ice/salt bath. When the temperature inside the flask reached 0° C., POCl3 (21 ml, 0.22 mol) was added slowly by the addition funnel. The inside temperature was not allowed to rise above 5° C. during the addition of the POCl3. When the addition of POCl3 was completed, the flask was placed on a steam bath for 2 hr. The flask was cooled to room temperature, then added slowly to a large excess of water (2 liters in a 4.5 liter beaker). The solution was stirred at room temperature for 3 hr, the solid was filtered off, washed repeatedly with water, and followed by washing with ethanol (20 ml). The product was recrystallized once from THF/water and dried at 60° C. in a vacuum oven for 6 hr. to produce 50 g (79% yield) of N-propylphenyl-3-formylcarbazole. 1H-N MR and IR spectra confirmed the structure of the product.

Workup

  1. customTo a 500 ml, three neck round bottom flask equipped with mechanical stirrer
  2. additionthermometer, and addition funnel
  3. customprepared
  4. customThe flask was placed in an ice/salt bath
  5. customreached 0° C.
  6. filtrationthe solid was filtered off
  7. washwashed repeatedly with water
  8. washby washing with ethanol (20 ml)
  9. customThe product was recrystallized once from THF/water
  10. customdried at 60° C. in a vacuum oven for 6 hr

Sources & evidence

ORD record
ord-9717dea986a3458bb2d9a6a8f3128ea4
Source dataset
uspto-grants-2002_01
Patent number
US06340548B1

Reaction notes

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