Water → HCID 13336842, compound

HRID 128381Notes

Reaction equation

HRID 128381 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].[CH:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([CH3:19])[CH:13]=1.[OH-].[Na+].O>CC(C)=O>[C:1]([C:3]1[C:8]([C:9]#[N:10])=[N:7][C:6]([O:18][C:17]2[CH:12]=[CH:13][C:14]([CH3:19])=[CH:15][CH:16]=2)=[CH:5][N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 14798Sodium HydroxideHCID 129071975-Chloropyrazine-2,3-dicarbonitrile

Product 1

HCID 13336842HCID 13336842, compoundYield 41.5%

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 5° C., and with stirring, a solution prepared from 0.54 g (0.005 mole) of p-cresol, 0.21 g (0.005 mole) of sodium hydroxide, 1 ml of water and 15 ml of acetone was added dropwise over the period of 15 minutes. The mixture was stirred at 0° to 5° C. for 1 hour. After the reaction, the solvent was removed by concentration under reduced pressure. The residue was extracted with 100 ml of chloroform. The chloroform solution was washed with 30 ml of a 1 N aqueous solution of sodium hydroxide and 30 ml of water and dried over anhydrous calcium chloride. Then, the solvent was distilled off. Recrystallization of the crude product from ethanol afforded 0.49 g (yield 41%) of 2,3-dicyano-5-(p-methylphenoxy)pyrazine.

Workup

  1. temperatureThe solution was cooled to 0° to 5° C.
  2. additionwas added dropwise over the period of 15 minutes
  3. stirringThe mixture was stirred at 0° to 5° C. for 1 hour
  4. customAfter the reaction
  5. customthe solvent was removed by concentration under reduced pressure
  6. extractionThe residue was extracted with 100 ml of chloroform
  7. washThe chloroform solution was washed with 30 ml of a 1 N aqueous solution of sodium hydroxide and 30 ml of water
  8. dry with materialdried over anhydrous calcium chloride
  9. distillationThen, the solvent was distilled off
  10. customRecrystallization of the crude product from ethanol

Sources & evidence

ORD record
ord-3727300682734555995d2e1faa600218
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Reaction notes

Loading…