Acrylonitrile → HCID 21201559, compound

HRID 1979288Notes

Reaction equation

HRID 1979288 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[CH:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1>CO>[N+:30]([C:29]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:23]([CH2:3][CH2:2][C:1]#[N:4])[C:20]1[CH:19]=[CH:18][CH:17]=[CH:22][CH:21]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 84072-NitrodiphenylamineHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 21201559HCID 21201559, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acrylonitrile (210 ml) and 40% benzyltrimethylammoniumhydroxide in methanol (1.5 ml) were added to 2-nitrodiphenylamine (100 g), and the mixture was refluxed with heat for one hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to thereby obtain 47.7 g of the titled compound as a red solid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heat for one hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c5c042c8a0d245d78defc248cc375240
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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