Sodium hydride → 4-Methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzenamine

HRID 53244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53244
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[NH2:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:10]=1[C:11](OC)=O>O1CCCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:9]([NH2:8])=[C:10]([C:11]2[O:7][N:6]=[C:3]([CH3:4])[N:5]=2)[CH:15]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 13052275Methyl 2-amino-5-methoxybenzoate

Produkt 1

HCID 199621234-Methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzenamineAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (594 mg) was added to a stirred suspension of acetamide oxime (1.0 g) and 4 molecular sieves (4 g) in dry tetrahydrofuran (50 ml) under nitrogen. The mixture was heated at 60° for 30 min then allowed to cool to room temperature. A solution of 2-amino-5-methoxybenzoic acid, methyl ester (2.0 g) in dry tetrahydrofuran (20 ml) was added and the mixture stirred at reflux for 2.5 h. The suspension was allowed to cool, filtered and the filtrate evaporated to give the title compound as a yellow solid (1.64 g)

Aufarbeitung

  1. temperatureThe mixture was heated at 60° for 30 min
  2. temperatureat reflux for 2.5 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-de14df84f908491bba4e59f0038f2dee
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618827

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