Dimethylformamide → Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate

HRID 1282398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1282398
CN(C)C=O.[NH2:6][C:7]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=1)=[CH:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:11]=1.Cl.NO>C(#N)C>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[O:22][N:6]=[C:7]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:28]=3)[CH:8]=2)=[CH:11][CH:12]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 443297Hydroxyamine hydrochlorideHCID 696777131-Amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene

Produkt 1

HCID 10737571Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoateAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dimethylformamide (44 ml), 1-amino-1-(4-methoxycarbonylphenyl)-3-oxo-3-(4-pentyloxyphenyl)-1-propene (5.5 g) and hydroxylamine hydrochloride (2.0 g) were charged in 300-ml three-necked flask at room temperature and heated, and the reaction was carried out at the inner temperature of 55 to 60° C. for 4 hours. After completion of the reaction, the mixture was cooled down to room temperature, and acetonitrile (110 ml) was added to separate the crystals. The inner temperature was made 0 to 5° C., and the crystals were filtered and washed with acetonitrile (28 ml) and water (110 ml). The crystals were dried overnight in vacuo to give methyl 4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoate (5.21 g)

Aufarbeitung

  1. temperatureheated
  2. customAfter completion of the reaction
  3. customto separate the crystals
  4. customwas made 0 to 5° C.
  5. filtrationthe crystals were filtered
  6. washwashed with acetonitrile (28 ml) and water (110 ml)
  7. customThe crystals were dried overnight in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1137a9ad34b14f2e9ba0c5523e8d7118
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455726B2

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