Dimethylformamide → 4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl cyanide

HRID 233277Notes

Reaction equation

HRID 233277 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1.[C-]#N.[K+].[CH3:27][N:28](C)C=O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][C:27]#[N:28])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 118095944-[2-(4-Chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazole

Product 1

HCID 109471004-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl cyanideYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl chloride (6.4 g), powdered potassium cyanide (4.0 g) and N,N-dimethylformamide (50 ml) was stirred for two hours at 60° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off to leave 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl cyanide (5.2 g, 81%). The product was recrystallized from ethyl acetate--hexane to afford colorless needles, m.p.109°-110° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6aabd8c155814be78b354befd4efde41
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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