Phenylacetonitrile → Benzeneacetamide

HRID 1621184Notes

Reaction equation

HRID 1621184 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:10].[Na+]>S(=O)(=O)(O)O>[C:2]1([CH2:1][C:8]([NH2:9])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8794PhenylacetonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 7680BenzeneacetamideYield 78%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Benzyl cyanide (5 g, 42.7 mmol) was added slowly to concentrated sulfuric acid (20 ml) cooled by water-ice bath. The solution was stirred overnight. The reaction mixture was poured into ice water and neutralized with 20% NaOH. The aqueous phase was extracted by ethyl acetate (3×15 mL). The combined organic layers were washed with water (3×10 mL) and brine (3×10 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate and hexane to give the title compound (4.5 g, 78%). 1H NMR (400 MHz, DMSO-d6) δ 7.54 (s, 1H), 7.20-7.32 (m, 5H), 6.87 (s, 1H), 3.38 (s, 2H).

Workup

  1. temperaturecooled by water-ice bath
  2. extractionThe aqueous phase was extracted by ethyl acetate (3×15 mL)
  3. washThe combined organic layers were washed with water (3×10 mL) and brine (3×10 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-de0140ba54c148889c98edbf8b411066
Source dataset
uspto-grants-2014_07
Patent number
US08772541B2

Reaction notes

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