Reacción #634741

ord-e427d33225a243589546ac43ff49d5ff

Ecuación de reacción

Cl
HCl
CC(=O)c1ccc(C(=O)O)cc1
4-Acetylbenzoic acid
N=C(N)NN.O=C(O)O
amino guanidine bicarbonate
→
C/C(=N\N=C(N)N)c1ccc(C(=O)O)cc1.Cl
4-[(1E)-N-(Diaminomethylene)ethanehydrazonoyl]benzoic acid hydrochloride

Reactantes

—
ArH
Cl
HCl
CC(=O)c1ccc(C(=O)O)cc1
4-Acetylbenzoic acid
N=C(N)NN.O=C(O)O
amino guanidine bicarbonate

Reactivos

Ninguno

Disolventes

CO
MeOH
CCOC(C)=O
EtOAc

Condiciones de reacción

Temperatura
20°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthe resulting precipitate was filtered
  2. 2
    Otroto give L2 (887 mg, 55%), mp (MeOH/EtOAc)>300° C.

Procedimiento

4-Acetylbenzoic acid (L1) (1.041 g, 6.34 mmol), amino guanidine bicarbonate (1.12 g, 8.2 mmol, 1.3 eq) and c.HCl (0.7 ml, 7.0 mmol) in MeOH (30 mL) was refluxed for 1 h. The reaction mixture was diluted with EtOAc cooled to 20° C. and the resulting precipitate was filtered and recrytallized from MeOH/EtOAc to give L2 (887 mg, 55%), mp (MeOH/EtOAc)>300° C.; 1H NMR ([(CD3)2SO] δ7.97-7.89 (m, 4 H, ArH), 6.75 (br, 4 H, 2×NH2), 2.25 (s, 3 H, CH3), mass APCI+ 221.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07939546B2uspto-grants-2011_05