Dimethylformamide → HCID 23437420, compound

HRID 900029Notes

Reaction equation

HRID 900029 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-b2b6d2fced544b5dbb2eff867dfb5495
Source dataset
uspto-grants-2008_04
Patent number
US07358014B2

Reaction notes

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