Acetonitrile → 4-(Cyanoacetyl)benzonitrile

HRID 1517205Notes

Reaction equation

HRID 1517205 reaction equation
[C:1](#[N:3])[CH3:2].[H-].[Na+].C[O:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1>O1CCCC1>[C:1]([CH2:2][C:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:7])#[N:3]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 70791Methyl 4-cyanobenzoate

Product 1

HCID 125401734-(Cyanoacetyl)benzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of acetonitrile (9.22 mL, 176 mmol) in tetrahydrofuran (320 mL) was added to sodium hydride (60% dispersion in mineral oil) (11.80 g, 294 mmol). This mixture was stirred at room temperature for 15 minutes, and then 4-Cyano-benzoic acid methyl ester (23.70 g, 147 mmol) was added. The reaction mixture was stirred at 60° C. for 2 hours, And then quenched onto an aqueous solution of hydrochloric acid (2M, 500 mL), and extracted with ethyl acetate (3×500 mL). The combined organic extracts were washed with brine (500 mL), dried over magnesium sulphate, filtered and evaporated under reduced pressure. This residue was triturated with 20% ethyl acetate in heptane to give the title compound as a solid (23.17 g, 93%). ESCI MS m/z 169 [M−H]−

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 2 hours
  2. customquenched onto an aqueous solution of hydrochloric acid (2M, 500 mL)
  3. extractionextracted with ethyl acetate (3×500 mL)
  4. washThe combined organic extracts were washed with brine (500 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThis residue was triturated with 20% ethyl acetate in heptane

Sources & evidence

ORD record
ord-df2c5c46bac1492b8e4934cf2ea2d8de
Source dataset
uspto-grants-2012_07
Patent number
US08232269B2

Reaction notes

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