Crystal and process for producing the same
a crystal and crystal technology, applied in the field of crystal production process, can solve the problems of difficult purification of compounds (i), and difficult removal of organic tin compounds, and achieve the effect of easy removal and difficult removal
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reference example 1
Synthesis of Methyl 2-[(2′-cyanobiphenyl-4-yl)methylamino]-3-nitrobenzoate[MBN]
[0264] 23 g of 2-(4-methylphenyl)benzonitrile [MPB], 22 g of N-bromosuccinic acid imide [NBS] and 47 mg of 2,2′-azobis(2,4-dimethylvaleronitrile) were suspended in 44 ml of dichoromethane, and the reaction was allowed to proceed at 45 to 50° C. for 5 hours under stirring. 46 ml of water was added, and the layers were separated to obtain organic layer (The same procedure was carried out three times totally). The organic layer was concentrated, and 50 ml of acetonitrile was added. The solution was concentrated again, and 50 ml of acetonitrile was added thereto to obtain 116 g of a solution of 2-(4-bromomethylphenyl)benzonitrile [BMB] in acetonitrile (yield calculated from a quantitated value of 2-(4-bromomethylphenyl)benzonitrile: 84%).
[0265] 30.1 g of methyl 2-tert-butoxycarbonylamino-3-nitrobenzoate [BAN], 40.8 g of potassium carbonate and 160 ml of acetonitrile were added to the acetonitrile solution in...
reference example 2
Synthesis of Methyl 2-carboxy-3-nitrobenzoate [MNA]
[0266] 3-Nitrophthalic acid [NPA] (660 kg), trimethyl orthoformate (400 kg), concentrated sulfuric acid (115 kg) and methanol (1180 kg) were mixed, and the mixture was stirred with heating (59 to 65° C.) for about 15 to 20 hours under reflux. The reaction solution was cooled, and concentrated at 40° C. or lower under reduced pressure. The residue was cooled to 30° C. or lower, water (900 L) was added, and the mixture was cooled to 5° C. or lower. The precipitated crystals were separated by a centrifuge, washed with water, and dried at 50° C. for about 50 hours to give methyl 2-carboxy-3-nitrobenzoate [MNA] (666.8 kg, 94.7%).
[0267] mp. 166-168° C.
[0268]1H-NMR (200 MHz, CDCl3) δ:4.03 (3H, s), 7.74 (1H, t), 8.39 (1H, dd), 8.42(1H, dd)
reference example 3
Synthesis of Methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN]
[0269] Methyl 2-carboxy-3-nitrobenzoate [MNA] obtained in Reference Example 2 (164 kg) was dissolved in dimethylformamide [DMF] (242 kg), diphenylphosphoryl azide [DPPA] (204 kg) was added thereto at room temperature, and triethylamine (87 kg) was added dropwise while maintaining at 20 to 35° C. After stirring at 20 to 30° C. for about 3 hours, t-butyl alcohol (930 kg) was added to the reaction solution. The temperature was risen to 85 to 90° C. over 3 to 5 hours, and the solution was stirred for 1 to 2 hours under reflux (85 to 90° C.). The reaction solution was cooled, concentrated, and the residue was dissolved in ethyl acetate (1400 L). The solution was washed successively with a mixture of 15% hydrochloric acid (160 L) and water (1890 L), water (660 L), 5% aqueous sodium bicarbonate solution (1100 kg) and water (660 L), and the organic layer was concentrated under reduced pressure. Methanol (300 kg) was added ther...
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