Water → HCID 13336842, compound

HRID 1462286Notes

Reaction equation

HRID 1462286 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 1N aqueous solution of sodium hydroxide and 30 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 1N aqueous solution of sodium hydroxide and 30 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-0e36a7602ffd4a009b34d59f7f959d8f
Source dataset
uspto-grants-1984_07
Patent number
US04460403

Reaction notes

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