Ammonium Chloride → 4-(1,2,4-Oxadiazol-3-yl)aniline

HRID 1665619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665619
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][O:14][N:13]=2)=[CH:8][CH:7]=1)([O-])=O>O.C1COCC1.[Zn]>[O:14]1[CH:15]=[N:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([NH2:3])=[CH:7][CH:8]=2)=[N:13]1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 27982883-(4-Nitrophenyl)-1,2,4-oxadiazole

Produkt 1

HCID 214837044-(1,2,4-Oxadiazol-3-yl)anilineAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ammonium chloride (214 mg, 4 mmol) in water (5 mL) was added to a stirred solution of 3-(4-nitro-phenyl)-[1,2,4]oxadiazole (200 mg, 1 mmol) in THF (15 mL). Zinc powder (262 mg, 4 mmol) was then added portion wise. The reaction was stirred at room temperature for 1 hour and then refluxed at 65° C. for 5 hours. The mixture was filtered over celite, the filtrate was evaporated and the residue was extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4 and evaporated to afford 155 mg (92%) of 4-[1,2,4]oxadiazol-3-yl-phenylamine. 1H NMR: (DMSO-d6): δ 9.5 (s, 1H), 7.7 (d, 2H), 6.7 (d, 2H), 5.8 (s, 2H).

Aufarbeitung

  1. temperaturerefluxed at 65° C. for 5 hours
  2. filtrationThe mixture was filtered over celite
  3. customthe filtrate was evaporated
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe ethyl acetate was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fd8a93ad09ba4013be5ac8549662c757
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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