Acrylonitrile → HCID 12926345, compound

HRID 893921Notes

Reaction equation

HRID 893921 reaction equation
[CH3:1][NH:2][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:18](#[N:21])[CH:19]=[CH2:20]>O1CCCC1>[C:18]([CH2:19][CH2:20][C:5]1([C:3](=[O:4])[NH:2][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:21]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 12926344HCID 12926344, compound

Product 1

HCID 12926345HCID 12926345, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 36.8 g. portion of 9-(N-methylcarbamoyl)fluorene was reacted with 10.6 g. of acrylonitrile in the presence of 10 g. of Triton B in tetrahydrofuran as described in Example 4. The reaction mixture was then concentrated under vacuum to a semi-solid, which was added to ice-water/ethyl acetate. The organic layer was separated, washed with water, and dried over sodium sulfate. The solution was evaporated to dryness to obtain 45.8 g. of crude product, which was crystallized from ethyl acetate/hexane to obtain 30 g. of the desired product, m.p. 185°-187°. Infrared analysis of the product showed a carbonyl band at 1685 cm-1 and a nitrile band at 2270 cm-1.

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum to a semi-solid, which
  2. additionwas added to ice-water/ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solution was evaporated to dryness
  7. customto obtain 45.8 g
  8. customof crude product, which was crystallized from ethyl acetate/hexane
  9. customto obtain 30 g

Sources & evidence

ORD record
ord-b7dc69c791ca483598404d58348da07e
Source dataset
uspto-grants-1981_08
Patent number
US04282170

Reaction notes

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