Hydrochloric Acid → HCID 178487771, Verbindung

HRID 552985

Reaktionsgleichung

Reaktionsgleichung von HRID 552985
C(C1NC=[CH:11][N:12]=1)(C1NC=CN=1)=O.CCCCCC.[C:19]([O:22][CH2:23][CH3:24])(=O)C.[OH2:25].Cl.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[OH:25][C:11]1[C:27]2[CH:28]=[CH:29][C:23]([O:22][CH3:19])=[CH:24][C:31]=2[O:30][N:12]=1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 178487771HCID 178487771, Verbindung

Versuchsvorschrift

A solution of carbonyl diimidazole (1.07 g, 6.57 mmol) in anhydrous THF (8 ml) was added to a stirred boiling solution of the hydroxamic acid (602 mg, 3.29 mmol) in THF (6 ml). The resulting solution was heated at reflux for approx. 8-10 hours, then allowed to cool to room temperature and stirred overnight under an argon atmosphere. Thin layer chromatography (tlc) (silica; 1:1 hexane/ethyl acetate) showed minimal starting material and new non polar material. The solution was evaporated on a rotary evaporator to give an orange colored oil. Water (6 ml) was added, and contents cooled (ice bath) and acidified to pH 2 with concentrated hydrochloric acid. The crude, damp 3-hydroxy-6-methoxy-1,2-benzisoxazole precipitated as a cream orange solid (645 mg).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for approx. 8-10 hours
  3. customThe solution was evaporated on a rotary evaporator
  4. customto give an orange colored oil
  5. temperaturecontents cooled (ice bath)
  6. customThe crude, damp 3-hydroxy-6-methoxy-1,2-benzisoxazole precipitated as a cream orange solid (645 mg)

Quellen und Nachweise

ORD-Eintrag
ord-b2c72d53edc04bb18924c02704202460
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951955B2

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