2-(Methylamino)ethanol → 7-Fluoro-2-[(2-hydroxyethyl)(methyl)amino]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17413
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C(N(C(C)C)CC)(C)C.[CH3:30][NH:31][CH2:32][CH2:33][OH:34]>ClCCl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:31]([CH2:32][CH2:33][OH:34])[CH3:30])=[N:6]2

Komponenten

5

Edukt 3

HCID 80162-(Methylamino)ethanol2×HCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685854957-Fluoro-2-[(2-hydroxyethyl)(methyl)amino]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.20 g, 0.70 mmol) was dissolved in dichloromethane (10 ml), and diisopropylethylamine (0.13 ml, 0.76 mmol) and N-methylethanolamine (62.0 μl, 0.78 mmol) were added. After heating under reflux for 3 hours, N-methylethanolamine (62.0 μl, 0.78 mmol) was added. After heated under reflux for 3 hours, this was diluted with dichloromethane. After washing with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1) to obtain a pale yellow oil (0.21 g, 93%).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter heated
  4. temperatureunder reflux for 3 hours
  5. washAfter washing with water
  6. dry with materialdrying over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-6af7a1412ed5469ab03933966d9e2f54
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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