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

HRID 128397

Reaction equation

HRID 128397 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-caroxyethyl)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-a2f9eef30b7e412db563be5317c91516
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Linked notes

Loading…