Dimethylamine → N,N,3,5-Tetramethyl-4-nitrobenzamide

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[C:1](N1C=CN=C1)([N:3]1C=CN=[CH:4]1)=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:26])[C:22]=1[N+:23]([O-:25])=[O:24])[C:17](O)=[O:18].CNC>O1CCCC1>[CH3:1][N:3]([CH3:4])[C:17](=[O:18])[C:16]1[CH:15]=[C:14]([CH3:13])[C:22]([N+:23]([O-:25])=[O:24])=[C:21]([CH3:26])[CH:20]=1

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실험 절차

1,1′-Carbonyldiimidazole (914 mg) is added to a solution of 3,5-dimethyl-4-nitrobenzoic acid (1 g) in tetrahydrofuran (10 mL). The mixture is stirred for 3 hours at room temperature, dimethylamine (7.7 mL, 2 M in tetrahydrofuran) is added and the mixture is stirred for further 30 minutes. After concentration the mixture is diluted with ethyl acetate and washed with hydrochloric acid (0.2 M), saturated aqueous NaHCO3 solution and brine. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 1 g; LC (method 20): tR=5.11 min; Mass spectrum (ESI+): m/z=223 [M+H]+.