Acrylic Acid → HCID 86738178, compound

HRID 1660302Notes

Reaction equation

HRID 1660302 reaction equation
[CH2:1]([N:4]([CH2:13][CH:14]=[CH2:15])[CH:5]=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH:2]=[CH2:3].[C:16]([OH:20])(=[O:19])[CH:17]=[CH2:18].C(OOC(=O)CCCCCCCCCCC)(=O)CCCCCCCCCCC>C(O)C>[C:16]([OH:20])(=[O:19])[CH:17]=[CH2:18].[CH2:1]([N:4]([CH:5]=[CH:6][CH:7]=[C:8]([C:9]#[N:10])[C:11]#[N:12])[CH2:13][CH:14]=[CH2:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6581Acrylic Acid5×HCID 7773Lauroyl peroxide5×HCID 53724731{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrile

Product 1

HCID 86738178HCID 86738178, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent5×

Procedure

60 g. of intermediate (A) and 20 g. of acrylic acid were diluted in 120 cc. of ethanol in a flask with stirrer and reflux and 2 g. of lauroyl peroxide were added, and then reflux heated. After one hour, 16 g. of acrylic acid and 1 g. of lauroyl peroxide diluted in 20 g. of ethanol were added; always continuing the reflux heating, at one hour time intervals the following additions were made: 13 g. of acrylic acid and 1 g. of lauroyl peroxide in 20 cc. of ethanol; 10 g. of acrylic acid and 0.8 g. of lauroyl peroxide in 15 cc. of ethanol; 8 g. of acrylic acid and 0.8 g. of lauroyl peroxide in 10 cc. of ethanol. After the last addition the mixture was refluxed for two hours, then it was cooled, and precipitated in ethyl ether; the precipitate was recovered on filter, washed with ether and vacuum dried at 50° C. The yield was 49 g. of a product containing about 23% of aminoallylidenemalononitrile units. The product was water and NaOH at pH=7 soluble. A solution at 6% 1:9000 diluted with water, had an optical density of 0.46.

Workup

  1. temperaturereflux
  2. temperatureheated
  3. temperatureheating, at one hour time intervals the following additions
  4. additionAfter the last addition the mixture
  5. temperaturewas refluxed for two hours
  6. temperatureit was cooled
  7. customprecipitated in ethyl ether
  8. customthe precipitate was recovered
  9. filtrationon filter
  10. washwashed with ether and vacuum
  11. customdried at 50° C
  12. additionof a product containing about 23% of aminoallylidenemalononitrile units
  13. additionA solution at 6% 1:9000 diluted with water

Sources & evidence

ORD record
ord-a0b8294ef8bb4614a6514ded73313b26
Source dataset
uspto-grants-1981_12
Patent number
US04307184

Reaction notes

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