三乙氧基乙酸乙酯

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

实验步骤: To a 50 mL round bottom flask at room temperature with a Teflon stir bar was added 6-chloropyrimidine-4,5-diamine (25 g, 172.9 mmol, 1 equiv), and anhydrous acetonitrile (300 mL). Ethyl 2,2,2-triethoxyacetate (36.87 g, 224.8 mmol, 36.9 mL, 1.3 equiv) followed by a catalytic quantity of 10-camphorsulfonic acid (3 g, 12.97 mmol, 0.075 equiv) were then added. The stirred reaction mixture was then heated to reflux for 16 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure to approximately 100 mL on a rotary evaporator and poured into 500 mL of vigorously stirring ice water. The resulting slurry was rapidly stirred for 20 minutes, and the resulting tan solid was then filtered through a medium porosity glass fritted funnel and was dried on the vacuum line to give the title compound as a brown solid (25.7 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.32 (broad s, 1H), 8.62 (s, 1H), 3.99 (s, 3H). MS (EI) for C7H5ClN4O2: 213 (MH+). were then added The stirred reaction mixture was then heated to reflux for 16 hours concentrated under reduced pressure to approximately 100 mL on a rotary evaporator poured into 500 mL of vigorously stirring ice water the resulting tan solid was then filtered through a medium porosity glass fritted funnel was dried on the vacuum line

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

实验步骤: To a 50 mL round bottom flask at room temperature with a Teflon stir bar was added 6-chloropyrimidine-4,5-diamine (25 g, 172.9 mmol, 1 equiv), and anhydrous acetonitrile (300 mL). Ethyl 2,2,2-triethoxyacetate (36.87 g, 224.8 mmol, 36.9 mL, 1.3 equiv) followed by a catalytic quantity of 10-camphorsulfonic acid (3 g, 12.97 mmol, 0.075 equiv) were then added. The stirred reaction mixture was then heated to reflux for 16 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure to approximately 100 mL on a rotary evaporator and poured into 500 mL of vigorously stirring ice water. The resulting slurry was rapidly stirred for 20 minutes, and the resulting tan solid was then filtered through a medium porosity glass fritted funnel and was dried on the vacuum line to give the title compound as a brown solid (25.7 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 13.32 (broad s, 1H), 8.62 (s, 1H), 3.99 (s, 3H). MS (EI) for C7H5ClN4O2: 213 (MH+). were then added The stirred reaction mixture was then heated to reflux for 16 hours concentrated under reduced pressure to approximately 100 mL on a rotary evaporator poured into 500 mL of vigorously stirring ice water the resulting tan solid was then filtered through a medium porosity glass fritted funnel was dried on the vacuum line

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-4-trifluoromethyl-benzenethiol (0.7 g) was added ethyl triethoxyacetate (3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 460 mg of 5-trifluoromethyl-benzothiazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-4-chloro-benzenethiol (1 g) was added ethyl triethoxyacetate (3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 392 mg of 5-chloro-benzothiazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-4-methylphenol (1 g, 8.1 mmol) was added ethyl triethoxyacetate (5.4 g, 3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 850 mg (91%) of 5-methyl-benzooxazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-3-methylphenol (1 g, 8.1 mmol) was added ethyl triethoxyacetate (5.4 g, 3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 1.36 g of 4-methyl-benzooxazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-aminophenol (437 mg, 4 mmol) was added ethyl triethoxyacetate (3.5 g, 4 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 516 mg of benzoxazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under nitrogen atmosphere, a mixture of 2-amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (6.67 g, 27.2 mmol) and ethyl triethoxyacetate (24.0 g, 54.4 mmol) was stirred at 130° C. for 15 hours. After cooling, n-hexane was added to the reaction liquid, and the precipitated solid was collected by filtration. The obtained solid was suspended and washed in diethyl ether to obtain the entitled compound (7.10 g, 80%) as a pale dark brown solid. After cooling the precipitated solid was collected by filtration washed in diethyl ether

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-4-trifluoromethyl-benzenethiol (0.7 g) was added ethyl triethoxyacetate (3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 460 mg of 5-trifluoromethyl-benzothiazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-4-chloro-benzenethiol (1 g) was added ethyl triethoxyacetate (3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 392 mg of 5-chloro-benzothiazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-4-methylphenol (1 g, 8.1 mmol) was added ethyl triethoxyacetate (5.4 g, 3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 850 mg (91%) of 5-methyl-benzooxazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 2-amino-3-methylphenol (1 g, 8.1 mmol) was added ethyl triethoxyacetate (5.4 g, 3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 1.36 g of 4-methyl-benzooxazole-2-carboxylic acid ethyl ester as a white solid. The reaction mixture was cooled triturated with hexane Filtration