苯溴马隆EP杂质C

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-water cooled suspension of NaH (0.18 g) in dry DMF (5 ml), is added a solution of a 2-ethyl-3-(4-hydroxybenzoyl)benzofuran, 1.00 g, in dry DMF 12 ml dropwise. After stirring for about 15 minutes running, chloroacetonitrile (0.24 ml) is added and heated up to 100° C. for 3 hours. After cooling to room temperature, the reaction mixture is poured over ice-water 100 ml and submitted to extraction by ethyl acetate. The solvent layer is washed by 10% NaOH solution and washed by NaCl solution and then dried by Na2CO3. Removing the solvent from the resulting solution gives a yellowish oily substance, that is 4-(2-ethyl-3-benzofuroyl)phenoxyacetonitrile. The obtained substance, in an amount of 1.05 g is dissolved in 15 ml of THF under an N2 gas stream. To this solution, aluminum chloride anhydride powder, 0.46 g, and then sodium azide, 0.98, are added and heated up to reflux for 24 hours. The reaction mixture is cooled by ice water and 10% HCl is added dropwise to make the solution acidic. After removal of THF, water is added and extracted by ethyl acetate (30 ml×2). The organic layer is washed by NaCl solution and dried over NaCO3. A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2. After cooling to room temperature submitted to extraction by ethyl acetate The solvent layer is washed by 10% NaOH solution washed by NaCl solution dried by Na2CO3 Removing the solvent from the resulting solution gives a yellowish oily substance, that heated up to reflux for 24 hours is added dropwise After removal of THF, water is added extracted by ethyl acetate (30 ml×2) The organic layer is washed by NaCl solution dried over NaCO3 A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-water cooled suspension of NaH (0.18 g) in dry DMF (5 ml), is added a solution of a 2-ethyl-3-(4-hydroxybenzoyl)benzofuran, 1.00 g, in dry DMF 12 ml dropwise. After stirring for about 15 minutes running, chloroacetonitrile (0.24 ml) is added and heated up to 100° C. for 3 hours. After cooling to room temperature, the reaction mixture is poured over ice-water 100 ml and submitted to extraction by ethyl acetate. The solvent layer is washed by 10% NaOH solution and washed by NaCl solution and then dried by Na2CO3. Removing the solvent from the resulting solution gives a yellowish oily substance, that is 4-(2-ethyl-3-benzofuroyl)phenoxyacetonitrile. The obtained substance, in an amount of 1.05 g is dissolved in 15 ml of THF under an N2 gas stream. To this solution, aluminum chloride anhydride powder, 0.46 g, and then sodium azide, 0.98, are added and heated up to reflux for 24 hours. The reaction mixture is cooled by ice water and 10% HCl is added dropwise to make the solution acidic. After removal of THF, water is added and extracted by ethyl acetate (30 ml×2). The organic layer is washed by NaCl solution and dried over NaCO3. A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2. After cooling to room temperature submitted to extraction by ethyl acetate The solvent layer is washed by 10% NaOH solution washed by NaCl solution dried by Na2CO3 Removing the solvent from the resulting solution gives a yellowish oily substance, that heated up to reflux for 24 hours is added dropwise After removal of THF, water is added extracted by ethyl acetate (30 ml×2) The organic layer is washed by NaCl solution dried over NaCO3 A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-water cooled suspension of NaH (0.18 g) in dry DMF (5 ml), is added a solution of a 2-ethyl-3-(4-hydroxybenzoyl)benzofuran, 1.00 g, in dry DMF 12 ml dropwise. After stirring for about 15 minutes running, chloroacetonitrile (0.24 ml) is added and heated up to 100° C. for 3 hours. After cooling to room temperature, the reaction mixture is poured over ice-water 100 ml and submitted to extraction by ethyl acetate. The solvent layer is washed by 10% NaOH solution and washed by NaCl solution and then dried by Na2CO3. Removing the solvent from the resulting solution gives a yellowish oily substance, that is 4-(2-ethyl-3-benzofuroyl)phenoxyacetonitrile. The obtained substance, in an amount of 1.05 g is dissolved in 15 ml of THF under an N2 gas stream. To this solution, aluminum chloride anhydride powder, 0.46 g, and then sodium azide, 0.98, are added and heated up to reflux for 24 hours. The reaction mixture is cooled by ice water and 10% HCl is added dropwise to make the solution acidic. After removal of THF, water is added and extracted by ethyl acetate (30 ml×2). The organic layer is washed by NaCl solution and dried over NaCO3. A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2. After cooling to room temperature submitted to extraction by ethyl acetate The solvent layer is washed by 10% NaOH solution washed by NaCl solution dried by Na2CO3 Removing the solvent from the resulting solution gives a yellowish oily substance, that heated up to reflux for 24 hours is added dropwise After removal of THF, water is added extracted by ethyl acetate (30 ml×2) The organic layer is washed by NaCl solution dried over NaCO3 A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-water cooled suspension of NaH (0.18 g) in dry DMF (5 ml), is added a solution of a 2-ethyl-3-(4-hydroxybenzoyl)benzofuran, 1.00 g, in dry DMF 12 ml dropwise. After stirring for about 15 minutes running, chloroacetonitrile (0.24 ml) is added and heated up to 100° C. for 3 hours. After cooling to room temperature, the reaction mixture is poured over ice-water 100 ml and submitted to extraction by ethyl acetate. The solvent layer is washed by 10% NaOH solution and washed by NaCl solution and then dried by Na2CO3. Removing the solvent from the resulting solution gives a yellowish oily substance, that is 4-(2-ethyl-3-benzofuroyl)phenoxyacetonitrile. The obtained substance, in an amount of 1.05 g is dissolved in 15 ml of THF under an N2 gas stream. To this solution, aluminum chloride anhydride powder, 0.46 g, and then sodium azide, 0.98, are added and heated up to reflux for 24 hours. The reaction mixture is cooled by ice water and 10% HCl is added dropwise to make the solution acidic. After removal of THF, water is added and extracted by ethyl acetate (30 ml×2). The organic layer is washed by NaCl solution and dried over NaCO3. A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2. After cooling to room temperature submitted to extraction by ethyl acetate The solvent layer is washed by 10% NaOH solution washed by NaCl solution dried by Na2CO3 Removing the solvent from the resulting solution gives a yellowish oily substance, that heated up to reflux for 24 hours is added dropwise After removal of THF, water is added extracted by ethyl acetate (30 ml×2) The organic layer is washed by NaCl solution dried over NaCO3 A solid substance obtained after removal of the organic solvent is recrystallized from CH2Cl2