Water → HCID 15523937, Verbindung

HRID 1978009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978009
[NH2:1][CH2:2][CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1.O>C1COCC1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:26])[NH:1][CH2:2]/[CH:3]=[C:4]2\[CH2:5][CH2:6][CH2:7][C:8]3[C:13]\2=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 794431-Isocyanato-4-methoxybenzeneHCID 54094556HCID 54094556, Verbindung

Produkt 1

HCID 15523937HCID 15523937, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-aminoethylidene)-7-methoxy-1,2,3,4-tetrahydronaphthalene (3.0 g, 14.8 mmol) in THF (20 ml) was gradually added dropwise, under ice cooling, 4-methoxyphenyl isocyanate (2.2 g, 14.8 mmol). The mixture was stirred for 30 minutes at room temperature. The reaction mixture was then poured into water. The organic layer was subjected to extraction with 10% methanol/chloroform. The extract solution was washed with brine and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=6:4), followed by recrystallization from ethyl acetate/methanol to give the above-titled compound (2.8 g, yield 54%).

Aufarbeitung

  1. extractionThe organic layer was subjected to extraction with 10% methanol/chloroform
  2. washThe extract solution was washed with brine and water, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=6:4)
  6. customfollowed by recrystallization from ethyl acetate/methanol

Quellen und Nachweise

ORD-Eintrag
ord-5427e51ea2b240dc9acc64354e2566d2
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235789B1

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