Acrylonitrile → HCID 12923589, compound

HRID 893920Notes

Reaction equation

HRID 893920 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]([CH:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:4].[C:19](#[N:22])[CH:20]=[CH2:21]>O1CCCC1>[C:19]([CH2:20][CH2:21][C:5]1([C:3](=[O:4])[N:2]([CH3:18])[CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)#[N:22]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 12926343HCID 12926343, compound

Product 1

HCID 12923589HCID 12923589, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 28 g. of portion of 9-(N,N-dimethylcarbamoyl)fluorene was added to a 3-liter flask, and 1 liter of tetrahydrofuran was added. The mixture was heated to 45°, and 10 ml. of Triton B was added. The mixture was stirred at constant temperature for 15 minutes, and then 8 g. of acrylonitrile was added in one portion. The mixture was then stirred at reflux temperature for 3 hours, and was cooled and concentrated under vacuum to obtain 51.8 g. of oil. The product was isolated as described in Example 1 and was recrystallized from hexane to obtain 15 g. of first-crop purified product, m.p. 109°-110°. Infrared analysis showed a characteristic carbonyl band at 1610 cm-1, and a characteristic nitrile band at 2220 cm-1.

Workup

  1. temperatureThe mixture was heated to 45°
  2. additionof Triton B was added
  3. stirringThe mixture was then stirred
  4. temperatureat reflux temperature for 3 hours
  5. temperaturewas cooled
  6. concentrationconcentrated under vacuum
  7. customto obtain 51.8 g
  8. customThe product was isolated
  9. customwas recrystallized from hexane
  10. customto obtain 15 g

Sources & evidence

ORD record
ord-0a87e256f55b4182be65aaab52465ea6
Source dataset
uspto-grants-1981_08
Patent number
US04282170

Reaction notes

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