Water → HCID 12905966, compound

HRID 128382Notes

Reaction equation

HRID 128382 reaction equation
[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6](Cl)=[CH:5][N:4]=1)#[N:2].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].O>CC(C)=O>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 129071975-Chloropyrazine-2,3-dicarbonitrile

Product 1

HCID 12905966HCID 12905966, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2,3-Dicyano-5-chloropyrazine (0.83 g; 0.005 mole) was dissolved in 25 ml of acetone. The solution was cooled to 0° to 3° C., and with stirring, a solution prepared from 0.55 g (0.005 mole) of thiophenol, 0.21 g (0.005 mole) of sodium hydroxide, 1 ml of water, and 20 ml of acetone was added dropwise over the period of 10 minutes. Then, the reaction mixture was worked up in the same way as in Example 7, and recrystallized from benzene to afford 0.57 g (yield 48%) of 2,3-dicyano-5-(phenylthio)pyrazine.

Workup

  1. temperatureThe solution was cooled to 0° to 3° C.
  2. additionwas added dropwise over the period of 10 minutes
  3. customrecrystallized from benzene

Sources & evidence

ORD record
ord-05ca50c4101945e495fcb561cc3fa16a
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Reaction notes

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