2-乙基苯甲腈

实验步骤: 投料

实验步骤: 投料

实验步骤: 投料: 将250 mL三口瓶置换氮气三次，加入M-C4X-22793-SM（5.00 g，38.20 mmol，1.00 eq）和超干四氢呋喃（40.00 mL，C=1.00 M），溶解澄清，降至-78℃，滴加乙基溴化镁（2.0 M in THF）（48.00 mL，96.02 mmol，2.50 eq），控温不高于-70℃，45 min加完，升至45℃反应。 反应3.5 h后，TLC（PE：DCM=10：1）监测，有中间产物的点，原料未消耗完，继续45℃反应，过夜。 第二天，TLC（PE：DCM=10：1）监测，原料消耗完全，停止反应。冰水浴下往反应液中逐滴加入浓盐酸（50.00 mL），加完后恢复室温反应。 反应3.0 h后，TLC（PE：DCM=10：1）监测，有产物点，中间产物未完全转化完，继续室温反应。 反应6.0 h后，TLC（PE：DCM=10：1）监测，产物点变浓，中间产物未完全转化完，继续室温反应，过夜。 第二天，TLC（PE：DCM=10：1）监测，中间产物完全转化为产物，停止反应。 冰水浴下，往反应液中滴加饱和碳酸氢钠溶液，加至不再有气泡产生为止，然后加入400.00 mL水和100.00 mL乙酸乙酯，静置，分层，取有机相，水相用乙酸乙酯萃取（100.00 mL*2），合并有机相，减压蒸馏除去溶剂后得到浅黄色液体15.00 g，里面包了大量THF但不影响下一步反应，不用纯化，直接投下一步。

实验步骤: 投料: 将250 mL三口瓶置换氮气三次，加入M-C4X-22793-SM（2.50 g，19.20 mmol，1.00 eq）和超干四氢呋喃（40.00 mL，C=0.50 M），溶解澄清，降至-78℃，滴加乙基溴化镁（2.0 M in THF）（24.00 mL，48.01 mmol，2.50 eq），控温不高于-70℃，15 min加完，升至45℃反应。 反应3.5 h后，TLC（PE：DCM=10：1）监测，有中间产物的点，原料未消耗完，继续45℃反应，过夜。 第二天，TLC（PE：DCM=10：1）监测，原料消耗完全，停止反应。冰水浴下往反应液中逐滴加入浓盐酸（25.00 mL），加完后恢复室温反应。 反应3.0 h后，TLC（PE：DCM=10：1）监测，有产物点，中间产物未完全转化完，继续室温反应。 反应6.0 h后，TLC（PE：DCM=10：1）监测，产物点变浓，中间产物未完全转化完，继续室温反应，过夜。 第二天，TLC（PE：DCM=10：1）监测，中间产物完全转化为产物，停止反应。 冰水浴下，往反应液中滴加饱和碳酸氢钠溶液，加至不再有气泡产生为止，然后加入150.00 mL水和50.00 mL乙酸乙酯，静置，分层，取有机相，水相用乙酸乙酯萃取（50.00 mL*2），合并有机相，减压蒸馏除去溶剂后得到橙色液体。不用纯化，直接投下一步。

实验步骤: 投料

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Lithium aluminum hydride (7.4 g 196 mmol) in tetrahydrofuran (130 mL) was slowly treated with 2-ethylbenzonitrile (4.99 g 38 mmol) in tetrahydrofuran (40 mL) at 0° C. under nitrogen. The mixture was stirred for 30 minutes at 0° C., 2 hours at room temperature, recooled to 0° C., and then slowly treated in succession with water (7.4 mL), 15% sodium hydroxide (7.4 mL) and water (22 mL). Additional tetrahydrofuran (50 mL) was added to facilitate stirring. The reaction mixture was filtered through celite, the filter cake was washed with tetrahydrofuran (150 mL), the filtrate was concentrated under reduced pressure, and the residue was partitioned between methylene chloride/saturated sodium chloride. The organic phase was dried (potassium carbonate), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (CDCl3) δ 1.24 (t, 3H), 2.69 (q, 2H), 3.89 (s, 2H), 7.20 (m, 3H), 7.32 (m, 1H). recooled to 0° C. to facilitate stirring The reaction mixture was filtered through celite the filter cake was washed with tetrahydrofuran (150 mL) the filtrate was concentrated under reduced pressure the residue was partitioned between methylene chloride/saturated sodium chloride The organic phase was dried (potassium carbonate) filtered the filtrate was concentrated under reduced pressure

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Lithium aluminum hydride (7.4 g 196 mmol) in tetrahydrofuran (130 mL) was slowly treated with 2-ethylbenzonitrile (4.99 g 38 mmol) in tetrahydrofuran (40 mL) at 0° C. under nitrogen. The mixture was stirred for 30 minutes at 0° C., 2 hours at room temperature, recooled to 0° C., and then slowly treated in succession with water (7.4 mL), 15% sodium hydroxide (7.4 mL) and water (22 mL). Additional tetrahydrofuran (50 mL) was added to facilitate stirring. The reaction mixture was filtered through celite, the filter cake was washed with tetrahydrofuran (150 mL), the filtrate was concentrated under reduced pressure, and the residue was partitioned between methylene chloride/saturated sodium chloride. The organic phase was dried (potassium carbonate), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (CDCl3) δ 1.24 (t, 3H), 2.69 (q, 2H), 3.89 (s, 2H), 7.20 (m, 3H), 7.32 (m, 1H). recooled to 0° C. to facilitate stirring The reaction mixture was filtered through celite the filter cake was washed with tetrahydrofuran (150 mL) the filtrate was concentrated under reduced pressure the residue was partitioned between methylene chloride/saturated sodium chloride The organic phase was dried (potassium carbonate) filtered the filtrate was concentrated under reduced pressure

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Lithium aluminum hydride (7.4 g 196 mmol) in tetrahydrofuran (130 mL) was slowly treated with 2-ethylbenzonitrile (4.99 g 38 mmol) in tetrahydrofuran (40 mL) at 0° C. under nitrogen. The mixture was stirred for 30 minutes at 0° C., 2 hours at room temperature, recooled to 0° C., and then slowly treated in succession with water (7.4 mL), 15% sodium hydroxide (7.4 mL) and water (22 mL). Additional tetrahydrofuran (50 mL) was added to facilitate stirring. The reaction mixture was filtered through celite, the filter cake was washed with tetrahydrofuran (150 mL), the filtrate was concentrated under reduced pressure, and the residue was partitioned between methylene chloride/saturated sodium chloride. The organic phase was dried (potassium carbonate), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (CDCl3) δ 1.24 (t, 3H), 2.69 (q, 2H), 3.89 (s, 2H), 7.20 (m, 3H), 7.32 (m, 1H). recooled to 0° C. to facilitate stirring The reaction mixture was filtered through celite the filter cake was washed with tetrahydrofuran (150 mL) the filtrate was concentrated under reduced pressure the residue was partitioned between methylene chloride/saturated sodium chloride The organic phase was dried (potassium carbonate) filtered the filtrate was concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 9.74 ml of 2-ethylbenzonitrile are added dropwise to 100 g of Na-X zeolite (Linde 13X, STREM) with vigorous stirring. After the exothermic reaction, 5.6 ml of bromine are added dropwise at 55° C., add vigorous stirring of the mixture is continued. The temperature is kept at 45-50° C., by means of an ice bath. After the addition is complete, the ice bath is removed, and the mixture is stirred at 50° C. for 20 hours. 300 ml of methanol are added to the reaction mixture while stirring and the suspension is clarified by filtration through Hyflow. The filtrate is evaporated and the residue is partitioned between 100 ml of ethyl acetate and 50 ml of saturated sodium bicarbonate solution. The organic phase is dried with sodium sulphate, filtered and evaporated. The title compound is obtained as a beige crystalline solid from the residue by flash chromatography. Rt=4.87. are added dropwise at 55° C. add vigorous The temperature is kept at 45-50° C., by means of an ice bath After the addition the ice bath is removed the mixture is stirred at 50° C. for 20 hours 300 ml of methanol are added to the reaction mixture while stirring the suspension is clarified by filtration through Hyflow The filtrate is evaporated the residue is partitioned between 100 ml of ethyl acetate and 50 ml of saturated sodium bicarbonate solution The organic phase is dried with sodium sulphate filtered evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5.0 g. of p-toluidine, 6.2 g. of o-ethylbenzonitrile and 6.3 g. of anhydrous aluminum chloride were heated at 120° C. with stirring for 1 hour. To the reaction mixture was added water and sodium hydroxide to make the mixture alkaline. The mixture was extracted with benzene and the extract was washed with water, dried and evaporated in vacuo to remove benzene. 10.2 g. (92% of theory) of N-(p-methylphenyl)-2-ethylbenzamidine was obtained. The mixture was extracted with benzene the extract was washed with water dried evaporated in vacuo to remove benzene

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5.0 g. of p-toluidine, 6.2 g. of o-ethylbenzonitrile and 6.3 g. of anhydrous aluminum chloride were heated at 120° C. with stirring for 1 hour. To the reaction mixture was added water and sodium hydroxide to make the mixture alkaline. The mixture was extracted with benzene and the extract was washed with water, dried and evaporated in vacuo to remove benzene. 10.2 g.(92% of theory) of N-(p-methylphenyl)-2-ethylbenzamidine was obtained. The mixture was extracted with benzene the extract was washed with water dried evaporated in vacuo to remove benzene