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

HRID 128396

Reaction equation

HRID 128396 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0ca0f74614af45378ca5b5ef88cf8ed7
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Linked notes

Loading…