3-Isoxazolamine, 5-(1,1-dimethylethyl)- → HCID 59674136, Verbindung

HRID 1391545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391545
Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=2[N:3]=1.[C:15]([C:19]1[O:23][N:22]=[C:21]([NH2:24])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>C(O)(C)C.Cl>[C:15]([C:19]1[O:23][N:22]=[C:21]([NH:24][C:2]2[N:6]([CH3:7])[C:5]3[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=3[N:3]=2)[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 2

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 108223912-Chloro-1-methyl-5-nitro-1H-benzimidazole

Produkt 1

HCID 59674136HCID 59674136, VerbindungAusbeute 317,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-Chloro-1-methyl-5-nitro-1H-benzoimidazole (200 mg, 0.19 mmol) and 5-tert-Butyl-isoxazol-3-ylamine (265 mg, 1.90 mmol) in isopropanol (15 ml) was added a solution of HCl (3 drops, 4.0 m in dioxane). The reaction was heated to 80° C. and after 20 h. the reaction mixture was cooled to rt. The solvent was evaporated to dryness and the resultant solid was dissolved in EtOAc and neutralized by a 10% NaHCO3 water solution. The combined organic layers were washed with water, dried over MgSO4 and concentrated to give a foam. The crude material was purified through silica gel to give the title compound as a yellow solid (190 mg, 63%). MS (ESI) m/z=316 [M+H].

Aufarbeitung

  1. temperaturewas cooled to rt
  2. customThe solvent was evaporated to dryness
  3. dissolutionthe resultant solid was dissolved in EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a foam
  8. customThe crude material was purified through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8b8b14432ed848cb861e07e5ab948fca
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338959B2

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