Реакция #725861

Уравнение реакции

aniline

HCl

dimethyl dihydroxyfumarate

→

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

Выход 65.0%

Растворители

methyl alcohol

Условия реакции

Обработка

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

Методика

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).

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