Реакция #215578

Уравнение реакции

hydrochloric acid

DL-α-amino-n-butyric acid

potassium hydroxide

2,3-Dicyano-5-chloro-6-phenylpyrazine

→

2,3-dicyano-5-(1-carboxy-n-propyl)amino-6-phenylpyrazine

Выход 86.0%

Растворители

water

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise over the period of 5 minutes
2. 2
   workup.STIRRINGThe mixture was then stirred at 30° C. for 30 minutes
3. 3
   ДругоеAfter the reaction
4. 4
   Температураthe reactor was cooled with ice
5. 5
   ЭкстракцияThe solution was then extracted with 100 ml of toluene
6. 6
   ПромывкаThe toluene layer was washed with 50 ml of a saturated aqueous solution of sodium chloride and 50 ml of water
7. 7
   Другоеthe solvent was removed by concentration under reduced pressure
8. 8
   Другоеto afford a yellowish white solid
9. 9
   ДругоеRecrystallization of the solid from ethanol

Методика

2,3-Dicyano-5-chloro-6-phenylpyrazine (2.41 g; 0.01 mole) was dissolved in 30 ml of tetrahydrofuran, and with stirring at 15° to 20° C., a solution prepared from 2.04 g (0.02 mole) of DL-α-amino-n-butyric acid, 1.12 g (0.02 mole) of potassium hydroxide and 40 ml of water was added dropwise over the period of 5 minutes. The mixture was then stirred at 30° C. for 30 minutes. After the reaction, the reactor was cooled with ice, and in the meanwhile, 2 ml of conc. hydrochloric acid was added to the reaction solution. The solution was then extracted with 100 ml of toluene. The toluene layer was washed with 50 ml of a saturated aqueous solution of sodium chloride and 50 ml of water, and the solvent was removed by concentration under reduced pressure to afford a yellowish white solid. Recrystallization of the solid from ethanol afforded 2.63 g (yield 86%) of 2,3-dicyano-5-(1-carboxy-n-propyl)amino-6-phenylpyrazine.

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