Acrylamide → HCID 86738169, compound

HRID 1660303Notes

Reaction equation

HRID 1660303 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].NC=CC=C(C#N)C#N>C(O)C>[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 6579Acrylamide5×HCID 53724731{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrileHCID 76223853HCID 76223853, compound

Product 1

HCID 86738169HCID 86738169, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent5×

Procedure

A solution of 120 g of acrylamide and 114 g of 3-diallylaminoallylidenmalononitrile (A) in 500 ml of ethanol was brought to reflux. 3.2 g of 2,2'-azobisisobutyrronitrile (AZBN) were added thereto and the mixture was left to reflux for 1 hour under stirring. A solution of 104 g of acrylamide, 800 ml of ethanol and 3.2 g of AZBN was then introduced therein. The obtained solution was left to reflux for 1 hour under stirring. A solution of 88 g of acrylamide, 400 ml of ethanol and 2.4 g of AZBN was introduced therein and the solution was left to reflux for 1 hour. A solution of 72 g of acrylamide, 400 ml of ethanol and 1.6 g of AZBN was added thereto and the obtained solution was left to reflux for 1 hour. A solution of 56 g of acrylamide, 400 ml of ethanol and 1.6 g of AZBN was finally added thereto and the obtained solution was left to reflux for 2 hours. The so-obtained mixture was cooled, filtered, washed with ethanol and then with ethyl ether and dried under vacuum at 50° C., thus obtaining 478 g of a water soluble product containing about 9% w/w of aminoallylidenmalononitrile moieties.

Workup

  1. temperatureto reflux
  2. addition3.2 g of 2,2'-azobisisobutyrronitrile (AZBN) were added
  3. waitthe mixture was left
  4. temperatureto reflux for 1 hour
  5. waitThe obtained solution was left
  6. temperatureto reflux for 1 hour
  7. stirringunder stirring
  8. waitthe solution was left
  9. temperatureto reflux for 1 hour
  10. waitthe obtained solution was left
  11. temperatureto reflux for 1 hour
  12. waitthe obtained solution was left
  13. temperatureto reflux for 2 hours
  14. temperatureThe so-obtained mixture was cooled
  15. filtrationfiltered
  16. washwashed with ethanol
  17. dry with materialwith ethyl ether and dried under vacuum at 50° C.
  18. customthus obtaining 478 g of a water soluble product

Sources & evidence

ORD record
ord-9f92470d065843769ea69b5cf97c08e2
Source dataset
uspto-grants-1981_12
Patent number
US04307183

Reaction notes

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