tert-Butanol → (-)-N-[1-(Methoxymethyl)propyl]-2,6-dinitro-3,4-xylidine
Reaktionsgleichung
C(O)(C)(C)C.[CH3:6][O:7][CH2:8][CH:9]([NH2:12])[CH2:10][CH3:11].Cl[C:14]1[C:15]([N+:25]([O-:27])=[O:26])=[C:16]([CH3:24])[C:17]([CH3:23])=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21]>C(Cl)(Cl)Cl>[CH3:6][O:7][CH2:8][CH:9]([NH:12][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:17]([CH3:23])=[C:16]([CH3:24])[C:15]=1[N+:25]([O-:27])=[O:26])[CH2:10][CH3:11]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
(-)-2-Amino-1-butanol [100 grams, prepared according to D. Pitre and E. B. Grabitz, Chimia 23, 399 (1969)] was added in a dropwise manner to a stirred solution of tert-butanol (800 ml.) containing potassium tert-butoxide (126 grams). After warming this mixture to 70° C. to 80° C. for 2 hours, methyl iodide (175 grams) was added slowly at temperatures below 50° C. The suspension which formed was then stirred with refluxing overnight. After removal of the solid phase by filtration, the filtrate was fractionally distilled to give (-)-1-(methoxymethyl)propylamine contaminated with traces of tert-butanol, boiling point 125° C. to 147° C./760 mm. This amine was then allowed to react with 4-chloro-3,5-di-nitro-o-xylene, as described earlier, to give the desired product as a bright yellow solid with melting point 42.5° to 44° C., [α]D25° =137.6° (c 2.504, chloroform).
Quellen und Nachweise
- ORD-Eintrag
- ord-d756adfe7f5942d8a2d789ac48ec1779
- Quelldatensatz
- uspto-grants-1979_08
- Patentnummer
- US04165231
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