{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrile → HCID 131712626, compound

HRID 1660306Notes

Reaction equation

HRID 1660306 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].[CH:16]([CH:18]1[O:22][C-:21]=[N:20][C:19]1=[O:23])=[CH2:17]>CN1CCCC1=O>[CH:16]([CH:18]1[O:22][C-:21]=[N:20][C:19]1=[O:23])=[CH2:17].[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

4

Reactant 2

HCID 53724731{3-[Di(prop-2-en-1-yl)amino]prop-2-en-1-ylidene}propanedinitrileHCID 131712625HCID 131712625, compound

Product 1

HCID 131712626HCID 131712626, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

25 g of intermediate (A) and 50 g of vinyloxazolidone were dissolved in 150 ml of N-methylpyrrolidone and added with 3.75 g of AZBN. The mixture was heated at 85° C. for 24 hours in a flask provided with stirrer and reflux condenser. The product was cooled, precipitated in ethyl ether (2 liters), washed with ether and dried. It was then redissolved in DMF and re-precipitated in ethyl ether. The yield was 32.7 g of a product soluble in water and dimethylformamide, containing about 37% w/w of aminoallylidenmalononitrile moieties.

Workup

  1. additionadded with 3.75 g of AZBN
  2. customprovided with stirrer
  3. temperaturereflux condenser
  4. temperatureThe product was cooled
  5. customprecipitated in ethyl ether (2 liters)
  6. washwashed with ether
  7. customdried
  8. dissolutionIt was then redissolved in DMF
  9. customre-precipitated in ethyl ether
  10. additionThe yield was 32.7 g of a product soluble in water and dimethylformamide, containing about 37% w/w of aminoallylidenmalononitrile moieties

Sources & evidence

ORD record
ord-24ac930cdd42442dbb6278c4027d596a
Source dataset
uspto-grants-1981_12
Patent number
US04307183

Reaction notes

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