DL-alanine → 2,3-Dicyano-5-(1-carboxyethyl)amino-6-phenylpyrazine

HRID 1462302Notes

Reaction equation

HRID 1462302 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][CH:19]([NH2:23])[C:20]([OH:22])=[O:21].[OH-].[Na+].O>CC(C)=O>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([NH:23][CH:19]([C:20]([OH:22])=[O:21])[CH3:18])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 602DL-alanineHCID 962WaterHCID 14798Sodium HydroxideHCID 129072055-Chloro-6-phenylpyrazine-2,3-dicarbonitrile

Product 1

HCID 133369692,3-Dicyano-5-(1-carboxyethyl)amino-6-phenylpyrazineYield 42%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3-Dicyano-5-chloro-6-phenylpyrazine (4.82 g; 0.02 mole) was dissolved in 50 ml of acetone. The solution was cooled to 0° to 5° C., and with stirring, a solution prepared from 1.78 g (0.02 mole) of DL-α-alanine, 1.64 g (0.02 mole) of sodium hydroxide and 40 ml of water was added dropwise over the period of 30 minutes. The mixture was worked up in the same way as in Example 23, and recrystallized from benzene to afford 2.46 g (yield 42%) of 2,3-dicyano-5-(1-carboxyethyl)amino-6-phenylpyrazine.

Workup

  1. temperatureThe solution was cooled to 0° to 5° C.
  2. additionwas added dropwise over the period of 30 minutes
  3. customrecrystallized from benzene

Sources & evidence

ORD record
ord-d738a542a3ef468e82c0ded71c5cb326
Source dataset
uspto-grants-1984_07
Patent number
US04460403

Reaction notes

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