Stannous Chloride → 3-(2,6-Dichlorophenyl)-5-(3-aminophenyl)-1,2,4-oxadiazole

HRID 860398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860398
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)[O:11][N:10]=1.O.O.[Sn](Cl)Cl.[Sn](Cl)Cl>C(OCC)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[O:11][N:10]=1

Komponenten

5

Edukt 3

HCID 24479Stannous ChlorideHCID 61436Stannous chloride dihydrateHCID 113596083-(2,6-Dichlorophenyl)-5-(3-nitrophenyl)-1,2,4-oxadiazole

Produkt 1

HCID 114609353-(2,6-Dichlorophenyl)-5-(3-aminophenyl)-1,2,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

The nitro oxadiazole prepared in Step 1 (200 mg) was dissolved in ethyl acetate (20 mL) and tin (II) chloride dihydrate (162 mg, 1.2 molar equivalent) was added. The mixture was stirred at room temperature for 1 h. An additional 1.2 molar equivalents of tin (II) chloride was added. After a further 4 h at room temperature, the reaction mixture was diluted with ethyl acetate and washed three times with water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired 3-(2,6-dichlorophenyl)-5-(3-aminophenyl)-1,2,4-oxadiazole as a white solid in quantitative yield. NMR (300 MHz, DMSO-d6): 7.70 (m, 3H), 7.36 (s, 1H), 7.24 (d, 2H), 6.91 (m, 1H), 5.57 ppm (broad s, 2H). LC-MS tr=33.1 min (Method W) MH+=307

Aufarbeitung

  1. waitAfter a further 4 h at room temperature
  2. washwashed three times with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ec5d3b458cfd4591872b410b52f3439b
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153880B2

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