Ethanol → 5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

HRID 1010834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010834
Cl.[NH2:2][OH:3].[OH-].[Na+].C(O)C.C(O[C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[C:13]([C:16]#[N:17])[C:14]#[N:15])C>O>[NH2:15][C:14]1[O:3][N:2]=[C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]=1[C:16]#[N:17]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27867012-(Ethoxy-phenyl-methylene)-malononitrile

Produkt 1

HCID 134495675-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Hydroxylamine hydrochloride was suspended in water (30 ml) and sodium hydroxide (4.4 g, 0.11 mole) and then ethanol (40 ml) was added, followed by batchwise addition of 2-(ethoxy-phenyl-methylene)-malononitrile (21.7 g, 0.11 mole). The reaction mixture was heated to 50° C. for 2 hours. The ethanol was removed under vacuum and the precipitate was filtered. The precipitate was redissolved in 50% ethyl acetate/hexanes and chromatographed on silica gel to give 8.2 g of product after removal of solvent (yield: 40%). The rest of the sequence was made by analogy to the methyl replacement of the phenyl analog.

Aufarbeitung

  1. customThe ethanol was removed under vacuum
  2. filtrationthe precipitate was filtered
  3. dissolutionThe precipitate was redissolved in 50% ethyl acetate/hexanes
  4. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1aa0bc934e8b447482546ca474dd12f9
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977342B2

Notizen zur Reaktion

Wird geladen…