Triethylamine → 2-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-5-(2-methoxy-phenyl)-[1,3,4]oxadiazole

HRID 2421158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421158
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[C:15]([OH:17])=O)[CH2:3][CH2:2]1.[CH3:18][O:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([NH:24][NH2:25])=O.[Cl-].ClC1N(C)C=C[N+]=1C.C(N(CC)CC)C>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:5]=2[C:15]2[O:17][C:22]([C:21]3[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=3[O:19][CH3:18])=[N:24][N:25]=2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24051o-AnisohydrazideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 223090805-Cyclopropyl-3-phenyl-1,2-oxazole-4-carboxylic acid

Produkt 1

HCID 167229072-(5-Cyclopropyl-3-phenyl-isoxazol-4-yl)-5-(2-methoxy-phenyl)-[1,3,4]oxadiazoleAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 5-cyclopropyl-3-phenyl-isoxazole-4-carboxylic acid (236 mg, 1.03 mmol) in dichloromethane (2 mL) were added 2-methoxybenzhydrazide (205 mg, 1.24 mmol), 2-chloro-1,3-dimethylimidazolium chloride (383 mg, 2.26 mmol) and triethylamine (0.52 ml, 5.15 mmol) at ambient temperature. The resulting suspension was stirred for 18 h at this temperature before diluting with dichloromethane (20 ml) and washing with water (20 mL) and brine (20 mL). The aqueous layers were extracted with dichlormethane and the combined organic layers dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20) afforded the title compound (121 mg, 33%) as a white solid. MS: m/e=360.2 [M+H]+.

Aufarbeitung

  1. washwashing with water (20 mL) and brine (20 mL)
  2. extractionThe aqueous layers were extracted with dichlormethane
  3. dry with materialthe combined organic layers dried over sodium sulfate
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20)

Quellen und Nachweise

ORD-Eintrag
ord-8db7792f09f3414b8d81fc4ead911587
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956074B2

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