2-[(4-Fluorophenoxy)methyl]oxirane → 5-(4-Fluoro-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 237732

Reaktionsgleichung

Reaktionsgleichung von HRID 237732
[N:1]#[C:2][NH2:3].[Na].[F:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)=[CH:8][CH:7]=1>CO>[F:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[O:13][C:2]([NH2:3])=[N:1][CH2:14]2)=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 27247922-[(4-Fluorophenoxy)methyl]oxiraneHCID 57375518Cyanamidnatrium

Produkt 1

HCID 685277115-(4-Fluoro-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of sodium hydrogen cyanamide (0.64 g, 10.0 mmol) in methanol (10 mL) was added dropwise 2-(4-fluoro-phenoxymethyl)-oxirane (1.68 g, 10 mmol) after which the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (50 mL) was added after which the resulting white precipitate was removed by filtration through celite and the filtrate concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 0.77 g (37%) of 5-(4-fluorophenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto remove methanol
  3. additionAnhydrous diethyl ether (50 mL) was added after which the resulting white precipitate
  4. customwas removed by filtration through celite
  5. concentrationthe filtrate concentrated
  6. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-ec006b5a2316419b869f56dac21cbb22
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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