2-Aminothiazole → 1-(2-Phenoxyphenyl)-5-(thiazol-2-yl)biuret
Reaktionsgleichung
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:24](=[O:29])=[N:25][C:26](Cl)=[O:27].[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>O1CCCC1>[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:24]([NH:25][C:26]([NH:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1)=[O:27])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
6
Reaktionsbedingungen
- Temperatur
- -30 °C
Versuchsvorschrift
To a solution of 2-phenoxyaniline (0.46 g, 2.50 mmol) in tetrahydrofuran (20 ml) was added diisopropylethylamine (0.89 ml, 5.00 mmol) and the solution was cooled to −30° C., then N-(chlorocarbonyl)isocyanate (0.3 ml, 3.75 mmol) was slowly added. The mixture was then allowed to warm up to the room temperature during 30 min. 2-Aminothiazole (0.375 g, 3.75 mmol) was added to the reaction mixture and stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure to afford crude product, which was purified by silica gel chromatography (hexanes:ethyl acetate from 80:20 to 30:70) to afford title compound (0.49 g, 55%) as pale yellow solid.
Aufarbeitung
- temperatureto warm up to the room temperature during 30 min
- concentrationThe reaction mixture was concentrated under reduced pressure
- customto afford crude product, which
- customwas purified by silica gel chromatography (hexanes:ethyl acetate from 80:20 to 30:70)
Quellen und Nachweise
- ORD-Eintrag
- ord-d34249aca5d74c04a60c3bc5072a013a
- Quelldatensatz
- uspto-grants-2011_11
- Patentnummer
- US08063081B2
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