N-(alpha-aromatic group-substituted-2-nitro-4,5-dialkoxybenzyloxycarbonyl)amine compound and method for producing same
A kind of technology of dialkoxybenzyloxycarbonyl and dimethoxybenzyloxycarbonyl, applied in the field of new compound N-amine compound, can solve problems such as no description
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Embodiment 1
[0156]
[0157] Dissolve 10.9 g of 2-nitro-4,5-dimethoxybenzaldehyde (Tokyo Chemical Co., Ltd.) in 150 ml of anhydrous tetrahydrofuran, cool to 0°C while stirring in a nitrogen stream, and add bromine dropwise over 15 minutes. 50 ml of tetrahydrofuran solution of phenylmagnesium (manufactured by 1 mol / L Aldrich).
[0158] After completion of the dropwise addition, 7.51 g of cyclohexyl isocyanate (Tokyo Chemical Co., Ltd.) was thrown into the reaction solution at room temperature, stirred for 5 hours, and left overnight.
[0159] Drop into the aqueous solution (using water 100ml) that is dissolved with ammonium chloride 3.2g the next day, after stirring for 10 minutes, extract with ethyl acetate, the organic phase is washed with saturated aqueous sodium bicarbonate solution, washed with water, and concentrated with an evaporator to obtain light yellow solid. The obtained solid was purified by column chromatography using a mixed solvent of hexane and ethyl acetate, and the di...
Embodiment 2
[0162]
[0163] Except having used 7.5 g of morpholine carbonyl chlorides instead of cyclohexyl isocyanate, it carried out similarly to Example 1, and obtained 9.6 g of light yellow crystals.
[0164] pass 1 H-NMR confirmed that the crystal was N-(α-phenyl-2-nitro-4,5-dimethoxybenzyloxycarbonyl)morpholine. The HPLC purity was 98 area%, and the isolated yield relative to 2-nitro-4,5-dimethoxybenzaldehyde was 47%. of the compound 1 The H-NMR spectrum is shown in figure 2 (3.4-3.7ppm8H OCH 2 CH 2 N, 3.9ppm 6H OCH 3 , 6.9ppm s 1H CH-O, 7.2-7.7ppm 7H aromatic CH). The UV absorption spectrum of this compound is shown in image 3 (1×10 -4 mol / L acetonitrile solution). According to the UV spectrum, the compound has absorption at 405nm. In addition, the measurement results of TG of this compound are shown in Figure 4 . The 5% weight reduction temperature of this compound was 233°C.
Embodiment 3
[0169]
[0170] The known compound α-phenyl-2-nitro-4,5-dimethoxybenzyl alcohol was synthesized with reference to Tetrahedron, 63, (2007), 474, and Molecules, 1999, 4, M113. 0.26 g of α-phenyl-2-nitro-4,5-dimethoxybenzyl alcohol and 0.17 g of cyclohexyl isocyanate were added to dehydrated toluene (30 ml) together with 0.06 g of dibutyltin dilaurate. It was reacted while heating under reflux for 10 hours.
[0171] The obtained reaction solution was concentrated, and the obtained solid was dissolved in dichloromethane (30 ml), washed with saturated brine (20 ml) and water (20 ml), the dichloromethane layer was concentrated, and reconstituted from ethanol. Crystallized to obtain 0.19 g of light yellow crystals.
[0172] pass 1 H-NMR confirmed that the crystal was N-(α-phenyl-2-nitro-4,5-dimethoxybenzyloxycarbonyl)cyclohexylamine. The HPLC purity was 98.5 area%, and the isolated yield relative to α-phenyl-2-nitro-4,5-dimethoxybenzyl alcohol was 50%.
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