Dimethylformamide → HCID 23437420, compound

HRID 2120029Notes

Reaction equation

HRID 2120029 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH2:11]([N:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:13][CH2:14][CH3:15]>O>[CH2:11]([N:16]1[C:17]2[CH:18]=[CH:19][C:20]([CH:3]=[O:4])=[CH:21][C:22]=2[C:23]2[C:28]1=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 5147738HCID 5147738, compound

Product 1

HCID 23437420HCID 23437420, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (100 mL) is stirred and cooled in an ice bath while phosphorus oxychloride (35 mL, 58 g, 0.38 mol) is gradually added. 9-Pentylcarbazole (52 g, 0.22 mol) is introduced and the resulting mixture is heated on a steam bath with stirring for 1.5 hours. The entire mixture is cooled and added to water (200 mL) and the crude product is filtered off at the pump, washed with water (200 mL). The crude product is recrystallized to form 9-pentyl-3-carbazolecarboxaldehyde.

Workup

  1. additionis gradually added
  2. temperaturethe resulting mixture is heated on a steam bath
  3. temperatureThe entire mixture is cooled
  4. filtrationthe crude product is filtered off at the pump
  5. washwashed with water (200 mL)
  6. customThe crude product is recrystallized

Sources & evidence

ORD record
ord-2fe64e70f1ee4c4c8c3759fee341540d
Source dataset
uspto-grants-2004_02
Patent number
US06689523B2

Reaction notes

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