Ethanol → HCID 86738169, compound

HRID 1660299Notes

Reaction equation

HRID 1660299 reaction equation
[C:1]([NH2:5])(=[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>O>[C:1]([NH2:5])(=[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

5

Reactant 3

HCID 702Ethanol5×HCID 6579Acrylamide5×HCID 53724731{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrile

Product 1

HCID 86738169HCID 86738169, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 120 g. of acrylamide and 114 g. of 3-diallylaminoallylidenemalononitrile (A) in 500 cc. of ethanol was refluxed. 3.2 g. of AZBN were added and the solution was refluxed for one hour under stirring. A solution of 104 g. of acrylamide, 800 cc. of ethanol and 3.2 g. of AZBN was added and the solution was refluxed for one hour under stirring. A solution of 88 g. of acrylamide, 400 cc. of ethanol and 2.4 g. of AZBN was added and refluxed for one hour. A solution of 72 g. of acrylamide, 400 cc. of ethanol and 1.6 g. of AZBN was added and the solution was refluxed for one hour. In conclusion a solution of 56 g. of acrylamide, 400 cc. of ethanol and 1.6 g. of AZBN was added and refluxed for 2 hours. The mixture was cooled, filtered, washed with ethanol and then with ethyl ether and vacuum dried at 50° C. 478 g. of a product containing about 9% aminoallylidenemalononitrile units in weight were obtained, the product solution at 6% in water diluted 1:2000 with water had an optical density of 0.76 at 382 nm.

Workup

  1. additionof AZBN were added
  2. temperaturethe solution was refluxed for one hour
  3. additionof AZBN was added
  4. temperaturethe solution was refluxed for one hour
  5. stirringunder stirring
  6. additionof AZBN was added
  7. temperaturerefluxed for one hour
  8. additionof AZBN was added
  9. temperaturethe solution was refluxed for one hour
  10. additionof AZBN was added
  11. temperaturerefluxed for 2 hours
  12. temperatureThe mixture was cooled
  13. filtrationfiltered
  14. washwashed with ethanol
  15. dry with materialwith ethyl ether and vacuum dried at 50° C
  16. additionof a product containing about 9% aminoallylidenemalononitrile units in weight
  17. customwere obtained

Sources & evidence

ORD record
ord-3fee23e315c044148688b8969c9d5fa9
Source dataset
uspto-grants-1981_12
Patent number
US04307184

Reaction notes

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