Acetone → HCID 10515403, 화합물

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CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:27]([O-:29])=[O:28])=[C:19]([NH:21][C:22]([CH3:26])([CH3:25])[CH2:23][OH:24])[CH:20]=1.CC(C)=O>C(O)(C)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:27]([O-:29])=[O:28])=[C:19]([NH:21][C:22]([CH3:26])([C:23]([OH:3])=[O:24])[CH3:25])[CH:20]=1

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실험 절차

Jones reagent (2.67 M) is added in aliquots (40 ml, 20 ml, 20 ml, 20 ml and 10 ml) every 15 min to a solution of 2-[N-(5-Chloro-2-nitrophenyl)]amino-2-methyl-1-propanol (IX,EXAMPLE 9, 26.9 g) and acetone (2.05 l) at 0° until the reaction is done as measured by TLC. Isopropanol (150 ml) is added and the mixture is allowed to warm to 20°-25°. The mixture is filtered and the solids are washed with acetone several tunes. The combined filtrates are concentrated and partitioned between ether (800 ml) and potassium hydroxide (10%, 3×100 ml). The basic layers are acidified (3 N hydrochloric acid) and extracted with methylene chloride (3×180 ml). The methylene chloride layers are dried over magnesium sulfate, filtered, and concentrated to provide the title compound, mp 146°-147°; IR (mineral oil) 3363, 2953, 2924, 2855, 1707, 1613, 1573, 1495, 1336, 1272, 1241 and 753 cm-1 ; NMR (CDCl3) 8.48, 8.16, 6.68, 6.64 and 1.74 δ; MS (EI, m/z) 258 and 213.