Diisopropylethylamine → 2-(N-tert-butyl-N-methylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17411

Reaktionsgleichung

Reaktionsgleichung von HRID 17411
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][C:32]([CH3:35])([CH3:34])[CH3:33]>ClCCl>[C:32]([N:31]([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)[CH3:30])([CH3:35])([CH3:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 84552N-Methyl-tert-butylamine2×HCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685839942-(N-tert-butyl-N-methylamino)-7-fluoro-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 (0.15 ml, 0.88 mmol) and N-methyl-tert-butylamine (0.10 ml, 0.84 mmol) were added. After heating under reflux for 3 hours, N-methyl-tert-butylamine (50.0 μl, 0.42 mmol) was added, followed by heating under reflux for 2 hours. This was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane) to obtain a pale yellow solid (0.22 g, 0.65 mmol, 93%).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperatureby heating
  4. temperatureunder reflux for 2 hours
  5. washwashed with water
  6. dry with materialdried 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)

Quellen und Nachweise

ORD-Eintrag
ord-0b6aaea06b77418ebe65367fb21e66c5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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