Ethanol → HCID 19705040, compound

HRID 846385Notes

Reaction equation

HRID 846385 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:13][C:14]#[N:15].[CH2:16]([O:18][C:19](=O)[O:20]CC)[CH3:17]>>[CH2:16]([O:18][C:19](=[O:20])[CH:13]([C:14]#[N:15])[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([Cl:12])[C:6]=1[Cl:5])[CH3:17]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 7766Diethyl CarbonateHCID 229020Benzeneacetonitrile, 2,3-dichloro-HCID 5360545Sodium2×

Product 1

HCID 19705040HCID 19705040, compound

Procedure

Sodium (1.2 g) was added portionwise to ethanol (50 ml) with stirring. After the sodium had dissolved a solution of 2,3-dichlorophenylacetonitrile (9.4 g) in diethylcarbonate (25 ml) was added dropwise. The reaction mixture was heated until EtOH distilled over. The rate of addition was controlled such that it equalled the rate of distillation. After the completion of the addition, the reaction mixture was heated and distilled for a further 4 hours. The cooled reaction mixture was partitioned between water and EtOAc (300 ml each). The organic layer was dried and evaporated in vacuo and the residue was purified by flash column chromatography to give the title product. (5 g, 39%).

Workup

  1. additionwas added dropwise
  2. distillationdistilled over
  3. additionThe rate of addition
  4. distillationthe rate of distillation
  5. additionAfter the completion of the addition
  6. temperaturethe reaction mixture was heated
  7. distillationdistilled for a further 4 hours
  8. customThe cooled reaction mixture
  9. customwas partitioned between water and EtOAc (300 ml each)
  10. customThe organic layer was dried
  11. customevaporated in vacuo
  12. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-1123e46bbf224b709f5e913854734618
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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