Reaktion #657214

ord-271a8c3dce49462ea99cf70ef5d32c70

Reaktionsgleichung

O=CC(=O)c1ccccc1
phenylglyoxal
O=S([O-])O.[Na+]
NaHSO3
[C-]#N.[Na+]
NaCN
NCCN
ethylenediamine
N#CC1=C(c2ccccc2)NCCN1
1,4,5,6-tetrahydro-3-phenyl-2-cyanopyrazine
Ausbeute 54.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONto dissolve virtually all solid material
  2. 2
    Temperaturthe mixture is heated at 50° C. for 30 minutes
  3. 3
    Temperaturcooled to about 10° C.

Vorschrift

13.8 parts of phenylglyoxal and 40 parts by volume of water are initially taken and heated to about 50° C., 61 parts of 38% strength aqueous NaHSO3 solution are introduced, and methanol is added in an amount sufficient to dissolve virtually all solid material. Thereafter, 6 parts of ethylenediamine are added at about 30° C., the mixture is heated at 50° C. for 30 minutes and then cooled to about 10° C., a solution of 5.2 parts of 95% pure NaCN in 13 parts by volume of water is added at this temperature, stirring is continued for a further 2 hours at room temperature and working up is carried out as described under Example 4. 10 parts (54% of theory) of 1,4,5,6-tetrahydro-3-phenyl-2-cyanopyrazine are obtained in the form of a reddish brown, viscous oil. The mass spectrum of this product shows the molecular peak expected for the empirical formula C11H11N3, at e/m=185, and its NMR spectrum exhibits the bands typical of the different NH groups, at about 3.5 ppm (N1 -H) and about 6.15 ppm (N4 -H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04734499uspto-grants-1988_03