Water → 5-(3-Chloro-thiophen-2-yl)-3-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazole

HRID 1823848

Reaktionsgleichung

Reaktionsgleichung von HRID 1823848
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].[F:10][C:11]([F:24])([F:23])[O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17](=[N:19]O)[NH2:18])=[CH:15][CH:14]=1.N1C=CC=CC=1.O>O1CCOCC1>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:8][N:19]=[C:17]([C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]([F:10])([F:23])[F:24])=[CH:22][CH:21]=2)[N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 27333094-(Trifluoromethoxy)benzamidoximeHCID 27358243-Chlorothiophene-2-carbonyl chloride

Produkt 1

HCID 101323925-(3-Chloro-thiophen-2-yl)-3-(4-trifluoromethoxy-phenyl)-[1,2,4]oxadiazoleAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-thiophene-2-carbonyl chloride (72.4 mg, 0.4 mmol) and 4-trifluoromethoxybenzamidoxime (88 mg, 0.4 mmol) in dioxane:pyridine (11 mL, 10:1) was refluxed for 10 h and cooled to room temperature. To the stirred solution was added 20 mL of water to produce precipitates. The solid was collected by filtration and washed with dioxane:water (1:3), and dried to yield 103 mg (75%) of the title compound. 1H NMR (CDCl3): 8.20 (d, J=9.0 Hz, 2H), 7.62 (d, J=5.4 Hz, 1H), 7.35 (bd, J=9.3 Hz, 2H), 7.14 (d, J=5.1 Hz, 1H).

Aufarbeitung

  1. customto produce
  2. customprecipitates
  3. filtrationThe solid was collected by filtration
  4. washwashed with dioxane:water (1:3)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0055c601091d416480dd187744127c33
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041685B2

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