Hydrochloric Acid → 6-Oxo-5-phenyl-1,6-dihydropyrazine-2,3-dicarbonitrile

HRID 128378

Reaction equation

HRID 128378 reaction equation
[NH2:1]/[C:2](/[C:7]#[N:8])=[C:3](\[NH2:6])/[C:4]#[N:5].[C:9]([C:17](O)=[O:18])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>>[C:4]([C:3]1[C:2]([C:7]#[N:8])=[N:1][C:17]([OH:18])=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1)#[N:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 11915Phenylglyoxylic AcidHCID 2723951Diaminomaleonitrile

Product 1

HCID 1785106496-Oxo-5-phenyl-1,6-dihydropyrazine-2,3-dicarbonitrileYield 90%

Procedure

Diaminomaleonitrile (5.40 g; 0.05 mole) and 7.50 g (0.05 mole) of benzoylformic acid were put into 50 ml of a 2 N aqueous solution of hydrochloric acid. The mixture was stirred at 20° to 30° C. for 30 minutes, and further stirred at 70° to 80° C. for 2 hours. The mixture was then cooled to room temperature. The precipitate formed was collected by filtration, washed thrice with 40 ml of water, and dried under reduced pressure to afford 10.0 g (yield 90%) of 2,3-dicyano-5-hydroxy-6-phenylpyrazine.

Workup

  1. stirringfurther stirred at 70° to 80° C. for 2 hours
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed thrice with 40 ml of water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d8e4c1a032884a0b9e9672ca6684bfb7
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Linked notes

Loading…