Methyl iodide → N-(5-tert-Butyl-1,2-oxazol-3-yl)-N,N',N'-trimethylurea

HRID 1764404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1764404
[CH3:1][N:2]([CH3:15])[C:3]([NH:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][N:7]=1)=[O:4].[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:1][N:2]([CH3:15])[C:3]([N:5]([CH3:18])[C:6]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:14])[CH3:13])[O:8][N:7]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 41648Isouron

Produkt 1

HCID 20534528N-(5-tert-Butyl-1,2-oxazol-3-yl)-N,N',N'-trimethylureaAusbeute 93,38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1,1-dimethyl-3-(5-t-butyl-3-isoxazolyl)-urea (10.99 g) in dry dimethylformamide (10 ml), 50% sodium hydride (2.75 g) is added at room temperature with stirring, and the resultant mixture is heated at 60° C for 15 minutes. A solution of methyl iodide (8.86 g) in dry dimethylformamide (30 ml) is added at 10° C in 1 hour thereto, and the mixture is heated at 80° C for 5 minutes and evaporated to remove the solvent. The residue is combined with water and shaken with chloroform. The chloroform layer is dried over anhydrous sodium sulfate and the solvent is evaporated. The residue is chromatographed on a column of silica gel to give 1,1,3-trimethyl-3-(5-t-butyl-3-isoxazolyl)-urea (10.94 g) as crystals melting at 90° to 91.0° C. The yield is 93.38%.

Aufarbeitung

  1. customevaporated
  2. customto remove the solvent
  3. stirringshaken with chloroform
  4. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  5. customthe solvent is evaporated
  6. customThe residue is chromatographed on a column of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-286293ad48284e129ecd5746a7987982
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04116671

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