Chloride → Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate

HRID 2098332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098332
[C:1]([NH:4][NH:5][C:6]([C:8]1[CH:32]=[CH:31][C:11]([O:12][C:13]2[CH:14]=[C:15]([CH:20]=[C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=1)=[O:7])(=O)[CH3:2].[Cl-]>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:21]1[CH:20]=[C:15]([CH:14]=[C:13]([O:12][C:11]2[CH:31]=[CH:32][C:8]([C:6]3[O:7][C:1]([CH3:2])=[N:4][N:5]=3)=[CH:9][CH:10]=2)[CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 312ChlorideHCID 66972175Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate2×

Produkt 1

HCID 66972395Methyl 3-(benzyloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirring mixture of Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate (Intermediate 10) (32 g, 73.7 mmol, 1 equiv.) in toluene in a single necked round bottomed flask fitted with reflux condenser and anhydrous CaCl2 guard tube, thonyl chloride (10.5 g, 88.4 mmol, 1.2 equiv.) was added carefully. The reaction mixture was refluxed until the reaction was complete. After completion, the reaction mixture was poured onto ice and extracted twice with ethyl acetate. The combined organic extracts was washed with brine and dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to give the title compound as yellow solid product (30 g).

Aufarbeitung

  1. customfitted
  2. temperaturewith reflux condenser and anhydrous CaCl2 guard tube
  3. temperatureThe reaction mixture was refluxed until the reaction
  4. additionAfter completion, the reaction mixture was poured onto ice
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organic extracts was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dc82125c886b4f9e8573f99224d81ea6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450494B2

Notizen zur Reaktion

Wird geladen…