Ethanol → HCID 18946314, compound

HRID 1768952Notes

Reaction equation

HRID 1768952 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C(O)C>O>[O:15]1[CH2:14][CH:13]1[CH2:11][NH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7835EpichlorohydrinHCID 770004-Aminophenylacetonitrile

Product 1

HCID 18946314HCID 18946314, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-aminobenzylcyanide (10 g, 75.7 mmol), epichlorohydrine (7.9 ml, 9.25 g, 100 mmol), ethanol (15 ml) and water (10 ml) was heated under reflux for 2 hours. After cooling the reaction mixture was poured into 100 ml of water and extracted with ether (3×50 ml). The organic extracts were combined and stirred with 50 ml of 10N NaOH at room temperature for 3 hours. The organic layer was separated, washed with water until neutral, dried over MgSO4 and concentrated. The residue was chromatographed over a silica gel column eluting with a 3:1 mixture of benzene and ethyl acetate to afford 7.24 g of the title compound as an oil, yield: 51.0%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with ether (3×50 ml)
  5. customThe organic layer was separated
  6. washwashed with water until neutral,
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was chromatographed over a silica gel column
  10. washeluting with a 3:1 mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-60aecbedda6d456b8a0875cd91e93612
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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