Boron trifluoride etherate → Methyl 2-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate

HRID 328115

Reaktionsgleichung

Reaktionsgleichung von HRID 328115
[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](Cl)=O.B(F)(F)F.CCOCC>O1CCOCC1>[CH3:11][O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:10][N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 69186N'-HydroxybenzenecarboximidamideHCID 11159939Methyl 2-(carbonochloridoyl)benzoate

Produkt 1

HCID 54140169Methyl 2-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 13.6 g. (0.1 mole) benzamide oxime in 625 milliliters dioxane is treated dropwise with 19.8 g. (0.1 mole) 2-chloroformyl benzoic acid methyl ester in 200 milliliters dioxane. This mixture is then refluxed for one hour, cooled slightly and treated with 3.3 milliliters of boron trifluoride etherate. The reaction mixture is refluxed for 18 hours. The resulting residue is cooled and filtered to remove a small amount of solid. The filtrate is evaporated in vacuo and the resulting oil is dissolved in ether, washed with water, 10 percent sodium carbonate, water and then brine. The ether solution is dried over anhydrous magnesium sulfate decolorized with charcoal filtered to remove the charcoal and the filtrate evaporated in vacuo to give o-(3-phenyl-1,2,4-oxadiazol-5-yl)-benzoic acid methyl ester.

Aufarbeitung

  1. temperatureThis mixture is then refluxed for one hour
  2. temperaturecooled slightly
  3. temperatureThe reaction mixture is refluxed for 18 hours
  4. temperatureThe resulting residue is cooled
  5. filtrationfiltered
  6. customto remove a small amount of solid
  7. customThe filtrate is evaporated in vacuo
  8. dissolutionthe resulting oil is dissolved in ether
  9. washwashed with water, 10 percent sodium carbonate, water
  10. dry with materialThe ether solution is dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customto remove the charcoal
  13. customthe filtrate evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b13b9028791545f88f56d4a75a3ed629
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04016170

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