Chloropyrazine → 2-Pyrazinyl-2-(2,4,6-trimethylphenyl)ethanenitrile

HRID 2299268Notes

Reaction equation

HRID 2299268 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11]#[N:12].Cl[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1.CC(C)([O-])C.[K+]>C1COCC1.[Cl-].[NH4+]>[N:15]1[CH:16]=[CH:17][N:18]=[CH:19][C:14]=1[CH:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:11]#[N:12]

Participants

6

Reactant 3

HCID 73277ChloropyrazineHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 183801732-Pyrazinyl-2-(2,4,6-trimethylphenyl)ethanenitrileYield 90.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-(2,4,6-trimethylphenyl)ethanenitrile (1.6 g) and chloro-pyrazine (1.6 g) in THF (6 mL) is slowly added dropwise to an ice-cold solution of potassium t-butoxide (3.4 g) in THF (10 mL). After the addition, the mixture is further stirred at 0° C. for 30 minutes and then diluted with aqueous ammonium chloride. The resulting mixture is extracted twice with ethyl ether and the combined extracts are washed with saturated brine, dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography (20 to 33% ethyl acetate in hexane) gives 2.15 g of the title compound as a beige solid 1H nmr (400 MHz, CDCl3) d 2.30 (s, 9 H), 5.78 (s, 1 H), 6.95 (s, 2 H), 8.46 (s, 1 H), 8.54 (d, 1 H), 8.60 (d, 1 H).

Workup

  1. additionAfter the addition
  2. extractionThe resulting mixture is extracted twice with ethyl ether
  3. washthe combined extracts are washed with saturated brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-029ddd8677314b5195a43de18f4fcd31
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

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