Reacción #725861

Ecuación de reacción

aniline

HCl

dimethyl dihydroxyfumarate

→

2,3-bis-(anilino)-but-2-enedioic acid dimethyl ester

Rendimiento 65.0%

Disolventes

methyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 3 hours
3. 3
   FiltraciónThe next morning, the resulting thick paste was filtered on a coarse frit
4. 4
   Lavadowashed with a 50% (v:v) methanol-water mixture
5. 5
   Otrodried in a vacuum oven
6. 6
   Otroyielding 30.1 g (65% yield) which
7. 7
   workup.ADDITIONa mixture of E/Z isomers (E:Z˜1:2)

Procedimiento

In a round bottom flask with a teflon stirbar, 25 g (142 mmol) of dimethyl dihydroxyfumarate (prepared according to a procedure described in U.S. Pat. No. 3,334,102), 29.0 g (312.5 mmol) of aniline, 0.1 mL of concentrated HCl, and 90 mL of methyl alcohol were mixed and heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and left overnight in a refrigerator. The next morning, the resulting thick paste was filtered on a coarse frit, washed with a 50% (v:v) methanol-water mixture, and dried in a vacuum oven, yielding 30.1 g (65% yield) which, according to NMR analysis, was a mixture of E/Z isomers (E:Z˜1:2).

Fuente