Hydrochloric Acid → 2,3-Dicyano-5-(1-carboxy-n-propyl)amino-6-phenylpyrazine

HRID 128396

반응식

HRID 128396 반응식
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6](Cl)=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1)#[N:2].[CH3:18][CH2:19][CH:20]([NH2:24])[C:21]([OH:23])=[O:22].[OH-].[K+].Cl>O1CCCC1.O>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([NH:24][CH:20]([C:21]([OH:23])=[O:22])[CH2:19][CH3:18])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1)#[N:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6657Alpha-Aminobutyric AcidHCID 14797Potassium HydroxideHCID 129072055-Chloro-6-phenylpyrazine-2,3-dicarbonitrile

생성물 1

HCID 133369702,3-Dicyano-5-(1-carboxy-n-propyl)amino-6-phenylpyrazine수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. additionwas added dropwise over the period of 5 minutes
  2. stirringThe mixture was then stirred at 30° C. for 30 minutes
  3. customAfter the reaction
  4. temperaturethe reactor was cooled with ice
  5. extractionThe solution was then extracted with 100 ml of toluene
  6. washThe toluene layer was washed with 50 ml of a saturated aqueous solution of sodium chloride and 50 ml of water
  7. customthe solvent was removed by concentration under reduced pressure
  8. customto afford a yellowish white solid
  9. customRecrystallization of the solid from ethanol

출처 및 근거

ORD 기록
ord-0ca0f74614af45378ca5b5ef88cf8ed7
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04259489

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