Reacción #643915

ord-ad9161cddaa149189ecdf649df4257e4

Ecuación de reacción

O=CC=Cc1cccn1-c1ccccc1[N+](=O)[O-]
4a
O=CC=Cc1cccn1-c1ccccc1[N+](=O)[O-]
3-[1-(2-Nitro-phenyl)-1H-pyrrol-2-yl]-propenal
N=C(N)NN.O=C(O)O
aminoguanidine bicarbonate
→
CC(=O)[O-].NC(=[NH2+])NN=CC=Cc1cccn1-c1ccccc1[N+](=O)[O-]
final product 5a
Rendimiento 55.0%
CC(=O)[O-].NC(=[NH2+])NN=CC=Cc1cccn1-c1ccccc1[N+](=O)[O-]
[1-(2-Nitrophenyl)-1H-pyrrol-2-yl-allylideneamino]guanidinium actate
Rendimiento 55.0%

Reactantes

O=CC=Cc1cccn1-c1ccccc1[N+](=O)[O-]
4a
O=CC=Cc1cccn1-c1ccccc1[N+](=O)[O-]
3-[1-(2-Nitro-phenyl)-1H-pyrrol-2-yl]-propenal
N=C(N)NN.O=C(O)O
aminoguanidine bicarbonate

Reactivos

Ninguno

Disolventes

C1CCOC1
THF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturarefluxed for 30 min
  2. 2
    OtroThe solvent was evaporated
  3. 3
    workup.ADDITIONthe residue was diluted with acetonitrile
  4. 4
    Otrothe product crystallised
  5. 5
    OtroPurification
  6. 6
    Otroby recrystallisation from acetonitrile

Procedimiento

2 g (8.3 mmol) 4a and 1.1 eqv. of aminoguanidine bicarbonate was mixed in THF and refluxed for 30 min. The solvent was evaporated and the residue was diluted with acetonitrile and the product crystallised. Purification by recrystallisation from acetonitrile yielded 1.35 g (55%) of the final product 5a (m.p. 192-194° C.).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08058306B2uspto-grants-2011_11