Ethylorthoformate → HCID 68125101, compound

HRID 596771Notes

Reaction equation

HRID 596771 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[CH:3][C:4](=[N:6][OH:7])[NH2:5].[CH:15]([O-])([O-])OCC>B(F)(F)F.CCOCC>[CH3:1][C:2]([C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)=[CH:3][C:4]1[N:5]=[CH:15][O:7][N:6]=1

Participants

4

Reactant 2

HCID 53630039EthylorthoformateHCID 54290087HCID 54290087, compound

Product 1

HCID 68125101HCID 68125101, compound

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

β-Methyl-p-chlorocinnamamidoxime (4.64 g.) was refluxed with ethyl orthoformate (50 ml.) and two drops of boron trifluoride etherate for 45 min. Ethyl orthoformate was removed under reduced pressure and the residual brown oil was dissolved in chloroform (100 ml.) and washed consecutively with 2N-hydrochloric acid (20 ml.), saturated sodium hydrogen carbonate solution (20 ml.), and water (20 ml.). The chloroform solution was evaporated to a brown oil (ca. 4.6 g.) which was chromatographed on silica gel. Elution with benzene gave 3-(β-methyl-p-chlorostyryl)-1,2,4-oxadiazole, 2.90 g. (60%), m.p. 56°-57°, λmax (EtOH) 273 nm (ε 20760) (Found: C 59.95; H, 4.2; Cl, 15.9; N, 12.7. C11H9ClN2O requires C, 59.85; H, 4.1; Cl, 16.1; N, 12.7%).

Workup

  1. customEthyl orthoformate was removed under reduced pressure
  2. dissolutionthe residual brown oil was dissolved in chloroform (100 ml.)
  3. washwashed consecutively with 2N-hydrochloric acid (20 ml.), saturated sodium hydrogen carbonate solution (20 ml.), and water (20 ml.)
  4. customThe chloroform solution was evaporated to a brown oil (ca. 4.6 g.) which
  5. customwas chromatographed on silica gel
  6. washElution with benzene

Sources & evidence

ORD record
ord-6549f721f48a46d1b909c35728b002c5
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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