Hydroxyamine hydrochloride → HCID 76543197, Verbindung

HRID 722317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722317
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([CH:29]=O)[C:13]2[O:18][CH:17]([C:19]([F:22])([F:21])[F:20])[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][C:14]=2[CH:28]=1>C(O)C.O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:29]=[N:2][OH:3])[C:13]2[O:18][CH:17]([C:19]([F:22])([F:21])[F:20])[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][C:14]=2[CH:28]=1

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21883599HCID 21883599, Verbindung

Produkt 1

HCID 76543197HCID 76543197, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel2×

Versuchsvorschrift

Hydroxylamine hydrochloride (1.30 g, 18.7 mmol), sodium acetate (1.50 g, 19.4 mmol), and a mixture of ethanol-water (80:20, 15 mL) were stirred at room temperature for 0.4 hours. The aldehyde (Example 76, Step 3) (3.07 g, 9.0 mmol) was dissolved in a solution of ethanol-water (4:1, 25 mL) and added to this mixture and stirred at 100° C. for 1 hour. The reaction was filtered hot and the filtrate allowed to cool to room temperature. An orange solid crystallized in the filtrate which was collected by vacuum filtration. The solid was dissolved in ethyl acetate and the solution washed with water, brine, dried over MgSO4, concentrated in vacuo. The resulting solid was recrystallized from ethyl acetate-hexane yielding the oxime as a tan powder (1.50 g, 47%): mp 186.6–187.6° C. 1H NMR (acetone-d6/300 MHz) 10.87 (s, 1H), 8.34 (s, 1H), 7.90 (s, 1H), 7.77 (d, 1H, J=2.6 Hz), 7.60 (d, 1H, J=2.6 Hz), 6.02 (q, 1H, J=7.1 Hz), 4.35 (m, 2H), 1.34 (t, 3H, J=7.0 Hz).

Aufarbeitung

  1. additionadded to this mixture
  2. stirringstirred at 100° C. for 1 hour
  3. filtrationThe reaction was filtered hot
  4. temperatureto cool to room temperature
  5. customAn orange solid crystallized in the filtrate which
  6. filtrationwas collected by vacuum filtration
  7. dissolutionThe solid was dissolved in ethyl acetate
  8. washthe solution washed with water, brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid was recrystallized from ethyl acetate-hexane yielding the oxime as a tan powder (1.50 g, 47%)

Quellen und Nachweise

ORD-Eintrag
ord-d5c42c68e5374f798ff8cad1af7e5e46
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138411B2

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