Phenylacetonitrile → HCID 66887401, compound

HRID 875230Notes

Reaction equation

HRID 875230 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11]1[C:12]([CH3:18])=[N:13][CH:14]=[C:15]([CH3:17])[N:16]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH4+].[Cl-]>O1CCCC1>[CH3:18][C:12]1[C:11]([CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]#[N:9])=[N:16][C:15]([CH3:17])=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 8794PhenylacetonitrileHCID 25517Ammonium ChlorideHCID 667713-Chloro-2,5-dimethylpyrazineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 66887401HCID 66887401, compoundYield 128.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl cyanide (2.00 g, 17.1 mmol) and 3-Chloro-2,5-dimethyl-pyrazine (2.03 g, 14.2 mmol) in tetrahydrofuran (100 mL) was added dropwise sodium bis-(trimethylsilyl)amide (1 M in THF, 35.6 mL, 35.6 mmol). After stirring at room temperature for 18 h, the reaction mixture was poured into sat. aq. NH4Cl (150 mL). After extraction with ethyl acetate (150 mL), the organic layer was washed with water (100 mL), dried over MgSO4 and concentrated in vacuo to afford (3,6-dimethylpyrazin-2-yl)(phenyl)acetonitrile [4.07 g, yield 96%; HPLC/MS: m/z=223 (M+H); log P(HCOOH)=2.28].

Workup

  1. extractionAfter extraction with ethyl acetate (150 mL)
  2. washthe organic layer was washed with water (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fde14280d584415b2d4480c31885789
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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