Hydroxyamine hydrochloride → 4-(2-Nitro-4-trifluoromethylbenzoyl)-5-methylisoxazole

HRID 2256877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256877
C(O[CH:4]=[C:5]([C:21](=[O:23])[CH3:22])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19])=[O:7])C.Cl.[NH2:25]O>C(O)C>[N+:18]([C:9]1[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:13][C:8]=1[C:6]([C:5]1[CH:4]=[N:25][O:23][C:21]=1[CH3:22])=[O:7])([O-:20])=[O:19]

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 537517422-Ethoxymethylene-1-(2-nitro-4-trifluoromethylphenyl)butan-1,3-dione

Produkt 1

HCID 538482954-(2-Nitro-4-trifluoromethylbenzoyl)-5-methylisoxazoleAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of crude 2-ethoxymethylene- 1-(2-nitro-4-trifluoromethylphenyl)butan-1,3-dione (13.25g) and hydroxylamine hydrochloride (3.7 g) in ethanol (80 ml) was stirred for 5 hours. The solution was evaporated almost to dryness and the resultant solution was diluted with ethyl acetate (100 ml). The solution was washed with water (3×40 ml), dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was triturated with a mixture of ether and petroleum spirit (bp 60°-80° C.) (1:1) and the resultant buff solid was filtered off. The solid was dissolved in dichloromethane (100 ml) and filtered through silica. The silica was washed with dichloromethane (100 ml) and the combined filtrates were evaporated to dryness to give 4-(2-nitro-4-trifluoromethylbenzoyl)-5-methylisoxazole (Compound 1,4.5 g) as an off-white solid mp 85°-86° C.

Aufarbeitung

  1. customThe solution was evaporated almost to dryness
  2. additionthe resultant solution was diluted with ethyl acetate (100 ml)
  3. washThe solution was washed with water (3×40 ml)
  4. dry with materialdried (anhydrous sodium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customThe residue was triturated with a mixture of ether and petroleum spirit (bp 60°-80° C.) (1:1)
  8. filtrationthe resultant buff solid was filtered off
  9. dissolutionThe solid was dissolved in dichloromethane (100 ml)
  10. filtrationfiltered through silica
  11. washThe silica was washed with dichloromethane (100 ml)
  12. customthe combined filtrates were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-11386b3248d849f8b9b4a764687ee8d7
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656573

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