Реакция #51297

Уравнение реакции

sodium bicarbonate

3,4-dichloroaniline

water

2-chloropropionic acid

water

→

title compound

N-(3,4-dichlorophenyl)alanine

Растворители

isopropanol

Условия реакции

Обработка

1. 1
   ДругоеN-(3,4-dichlorophenyl)alanine was prepared
2. 2
   Температураbefore heating
3. 3
   Температураunder reflux for 4-5 days
4. 4
   ТемператураAfter cooling
5. 5
   Другоеthe unreacted 3,4-dichloroaniline is removed by filtration
6. 6
   Фильтрацияthe resultant precipitate is filtered
7. 7
   Промывкаwashed
8. 8
   Другоеdried

Методика

Using the procedure set forth in U.S. Pat. No. 3,598,859, the disclosure of which is incorporated herein by reference in its entirety. N-(3,4-dichlorophenyl)alanine was prepared. Specifically, to a solution of 3,4-dichloroaniline (1 equivalent) (Aldrich) in isopropanol (about 500 mL per mole of 3,4-dichloroaniline) is added water (about 0.06 mL per mL of isopropanol) and 2-chloropropionic acid (2 equivalents) (Aldrich). This mixture is warmed to 40° C. and sodium bicarbonate (0.25 equivalents) is added in successive portions before heating under reflux for 4-5 days. After cooling, the reaction mixture is poured into water and the unreacted 3,4-dichloroaniline is removed by filtration. The filtrate is acidified to pH 3-4 with concentrated hydrochloric acid and the resultant precipitate is filtered, washed and dried to yield the title compound, m.p.=148-149° C.

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