Acrylic Acid → HCID 86738176, compound

HRID 1660301Notes

Reaction equation

HRID 1660301 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]([N:9](CC=C)[CH:10]=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15])[CH:7]=[CH2:8]>C(O)C>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]([NH:9][CH:10]=[CH:11][CH:12]=[C:13]([C:14]#[N:15])[C:16]#[N:17])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 53724731{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrile

Product 1

HCID 86738176HCID 86738176, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 60 g.=56 cc. of acrylic acid and 60 g. of 3-diallylaminoallylidenemalononitrile (A) in 250 cc. of ethanol was refluxed. 6 g. of AZBN were added and it was reflux-washed for 18 hours. It was cooled, saturated with ether and precipitated in ether, washed with ether and vacuum dried at 50° C. The yield was 92 g. of a product containing about 27% of aminoallylidenemalononitrile units in weight, whose solution at 6% in water and NaOH at pH7 was diluted at 1:8000 with water had an optical density of 0.60 at 382 nm. All subsequent optical density readings are given at this wavelength unless otherwise stated.

Workup

  1. additionof AZBN were added
  2. washit was reflux-washed for 18 hours
  3. temperatureIt was cooled, saturated with ether
  4. customprecipitated in ether
  5. washwashed with ether and vacuum
  6. customdried at 50° C
  7. additionof a product containing about 27% of aminoallylidenemalononitrile units in weight, whose solution at 6% in water
  8. additionNaOH at pH7 was diluted at 1:8000 with water

Sources & evidence

ORD record
ord-b6e852178ea8478ca1809516327cdb58
Source dataset
uspto-grants-1981_12
Patent number
US04307184

Reaction notes

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