Dimethylformamide → Methanone, phenylpyrazinyl-

HRID 223124Notes

Reaction equation

HRID 223124 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](=NO)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+].ClCC#N.CN(C)C=[O:25]>>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:25]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 136408870HCID 136408870, compound

Product 1

HCID 137933Methanone, phenylpyrazinyl-

Procedure

Phenyl pyrazinyl ketone oxime (8.0 g) was stirred in 100 ml of dimethyl formamide containing 2.0 g of a 50% dispersion of sodium hydride in oil, for 0.5 hours at room temperature. Chloroacetonitrile (2.7 g) was added. The reaction mixture was stirred for 1 hour. The greater part of the dimethylformamide was evaporated under reduced pressure and the residue was treated with ether and water. The ether layer was separated and dried over magnesium sulphate. The product was recrystallized from a mixture of ether and petroleum ether (40°-60° C.), yielding pure phenyl pyrazinyl ketone, O-cyanomethyl oxime (5.6 g, m.p. 87°-89° C.).

Workup

  1. customThe greater part of the dimethylformamide was evaporated under reduced pressure
  2. additionthe residue was treated with ether and water
  3. customThe ether layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customThe product was recrystallized from a mixture of ether and petroleum ether (40°-60° C.)

Sources & evidence

ORD record
ord-3119c6306df647be825b0190ee47e867
Source dataset
uspto-grants-1982_10
Patent number
US04352804

Reaction notes

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