Reacción #833218

Ecuación de reacción

2,6-dichloro-3-nitrobenzaldehyde

Aminoguanidine hydrogen carbonate

hydrochloric acid

→

(2,6-dichloro-3-nitrobenzylideneamino)-guanidine hydrochloride

Disolventes

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturathe mixture heated
3. 3
   Temperaturaunder reflux for 7 h
4. 4
   OtroThe solution was evaporated under reduced pressure
5. 5
   Temperaturain refluxing ethanol
6. 6
   workup.ADDITIONby addition of dilute sodium hydroxide solution
7. 7
   Temperaturacooled
8. 8
   Otroto yield a white solid which
9. 9
   Otrowas collected
10. 10
    workup.DISSOLUTIONThis solid was dissolved in hot methanol
11. 11
    workup.ADDITIONdiluted with diethyl ether
12. 12
    Temperaturacooled

Procedimiento

Aminoguanidine hydrogen carbonate (1.24 g, 9.1 mmol) was added to a solution of concentrated hydrochloric acid (0.8 cm3, 9.3 mmol) in water (3 cm3). After diluting the resulting solution with ethanol (20 cm3), 2,6-dichloro-3-nitrobenzaldehyde (2.0 g, 9.1 mmol) was added and the mixture heated under reflux for 7 h. The solution was evaporated under reduced pressure and the residual solid suspended in refluxing ethanol, basified (pH 11) by addition of dilute sodium hydroxide solution and cooled to yield a white solid which was collected. This solid was dissolved in hot methanol and the solution acidified (pH 2) with ethanolic hydrogen chloride, diluted with diethyl ether and cooled to yield (2,6-dichloro-3-nitrobenzylideneamino)-guanidine hydrochloride as a white solid, m.p. 186°-7° C.

Fuente