氯唑沙宗杂质N1

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: A solution of N-(5-chloro-2-hydroxyphenyl)urea (0.9 g, 4.9 mmol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.0 g, 3.8 mmol) in dimethylformamide were stirred under nitrogen. Cesium carbonate (1.9 g, 5.7 mmol) was added to the mixture and the reaction was stirred under nitrogen at room temperature over night. The mixture was partitioned between water and dichloromethane, and the organic phase was washed with water. After drying, filtration and evaporation of the solvent 0.48 g, (52%) of subtitle compound was obtained. The mixture was partitioned between water and dichloromethane the organic phase was washed with water After drying filtration and evaporation of the solvent 0.48 g, (52%) of subtitle compound was obtained

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

实验步骤: A solution of N-(5-chloro-2-hydroxyphenyl)urea (0.9 g, 4.9 mmol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.0 g, 3.8 mmol) in dimethylformamide were stirred under nitrogen. Cesium carbonate (1.9 g, 5.7 mmol) was added to the mixture and the reaction was stirred under nitrogen at room temperature over night. The mixture was partitioned between water and dichloromethane, and the organic phase was washed with water. After drying, filtration and evaporation of the solvent 0.48 g, (52%) of subtitle compound was obtained. The mixture was partitioned between water and dichloromethane the organic phase was washed with water After drying filtration and evaporation of the solvent 0.48 g, (52%) of subtitle compound was obtained

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

实验步骤: 2-amino-4-chlorophenol (1.3 g, 8.9 mmol) was dissolved in 1M HCl (10 mL). Ammonium acetate was added to the solution to adjust pH to 5. The stirred mixture was treated with a suspension of potassium cyanate (0.80 mg, 9.8 mmol) in water, and than kept overnight at room temperature. Water was removed by evaporation and the residue was recrystallized from water to afford pink precipate (0.9 g, 55%). Water was removed by evaporation the residue was recrystallized from water to afford pink precipate (0.9 g, 55%)

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

实验步骤: 2-amino-4-chlorophenol (1.3 g, 8.9 mmol) was dissolved in 1M HCl (10 mL). Ammonium acetate was added to the solution to adjust pH to 5. The stirred mixture was treated with a suspension of potassium cyanate (0.80 mg, 9.8 mmol) in water, and than kept overnight at room temperature. Water was removed by evaporation and the residue was recrystallized from water to afford pink precipate (0.9 g, 55%). Water was removed by evaporation the residue was recrystallized from water to afford pink precipate (0.9 g, 55%)

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

实验步骤: A suspension of N-(5-chloro-2-hydroxyphenyl)urea (53 mg, 0.28 mmol), cesium carbonate (92 mg, 0.28 mmol) and epibromohydrine (49 mg, 0.36 mmol) in dry DMF (0.6 mL) was stirred at room temperature for 24 hours. The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water three times, dried and concentrated to a solid residue. This crude product was recrystallized (ethyl ether and heptane to afford the subtitle compound (18 mg, 26.5%). The mixture was then partitioned between ethyl acetate and water The organic phase was washed with water three times dried concentrated to a solid residue This crude product was recrystallized (ethyl ether and heptane

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

实验步骤: A suspension of N-(5-chloro-2-hydroxyphenyl)urea (53 mg, 0.28 mmol), cesium carbonate (92 mg, 0.28 mmol) and epibromohydrine (49 mg, 0.36 mmol) in dry DMF (0.6 mL) was stirred at room temperature for 24 hours. The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water three times, dried and concentrated to a solid residue. This crude product was recrystallized (ethyl ether and heptane to afford the subtitle compound (18 mg, 26.5%). The mixture was then partitioned between ethyl acetate and water The organic phase was washed with water three times dried concentrated to a solid residue This crude product was recrystallized (ethyl ether and heptane

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

实验步骤: A solution of potassium cyanate (6.14 g, 75.6 mmol) in water (50 mL) was added dropwise to a stirred suspension of 2-amino-4-chlorophenol (5.00 g, 34.8 mmol) in a mixture of acetic acid (350 mL) and water (250 mL) and the resulting solution was stirred at room temperature for 3 hours. The reaction mixture was extracted three times with ethyl ether. The ether extracts were combined and concentrated to a thick oil. A 10% solution of sodium hydrogen carbonate (250 mL) was added to the above oil. The solid product was filtered and washed several times with water and recrystallized (toluene containing a little methanol) to afford the subtitle compound (3.27 g, 50.4%). The reaction mixture was extracted three times with ethyl ether concentrated to a thick oil A 10% solution of sodium hydrogen carbonate (250 mL) was added to the above oil The solid product was filtered washed several times with water recrystallized (toluene containing a little methanol)

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

实验步骤: A suspension of N-(5-chloro-2-hydroxyphenyl)urea (53 mg, 0.28 mmol), cesium carbonate (92 mg, 0.28 mmol) and epibromohydrine (49 mg, 0.36 mmol) in dry DMF (0.6 mL) was stirred at room temperature for 24 hours. The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water three times, dried and concentrated to a solid residue. This crude product was recrystallized (ethyl ether and heptane to afford the subtitle compound (18 mg, 26.5%). The mixture was then partitioned between ethyl acetate and water The organic phase was washed with water three times dried concentrated to a solid residue This crude product was recrystallized (ethyl ether and heptane

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

实验步骤: A solution of potassium cyanate (6.14 g, 75.6 mmol) in water (50 mL) was added dropwise to a stirred suspension of 2-amino-4-chlorophenol (5.00 g, 34.8 mmol) in a mixture of acetic acid (350 mL) and water (250 mL) and the resulting solution was stirred at room temperature for 3 hours. The reaction mixture was extracted three times with ethyl ether. The ether extracts were combined and concentrated to a thick oil. A 10% solution of sodium hydrogen carbonate (250 mL) was added to the above oil. The solid product was filtered and washed several times with water and recrystallized (toluene containing a little methanol) to afford the subtitle compound (3.27 g, 50.4%) The reaction mixture was extracted three times with ethyl ether concentrated to a thick oil A 10% solution of sodium hydrogen carbonate (250 mL) was added to the above oil The solid product was filtered washed several times with water recrystallized (toluene containing a little methanol)

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

实验步骤: A solution of potassium cyanate (6.14 g, 75.6 mmol) in water (50 mL) was added dropwise to a stirred suspension of 2-amino-4-chlorophenol (5.00 g, 34.8 mmol) in a mixture of acetic acid (350 mL) and water (250 mL) and the resulting solution was stirred at room temperature for 3 hours. The reaction mixture was extracted three times with ethyl ether. The ether extracts were combined and concentrated to a thick oil. A 10% solution of sodium hydrogen carbonate (250 mL) was added to the above oil. The solid product was filtered and washed several times with water and recrystallized (toluene containing a little methanol) to afford the subtitle compound (3.27 g, 50.4%) The reaction mixture was extracted three times with ethyl ether concentrated to a thick oil A 10% solution of sodium hydrogen carbonate (250 mL) was added to the above oil The solid product was filtered washed several times with water recrystallized (toluene containing a little methanol)

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

实验步骤: A suspension of N-(5-chloro-2-hydroxyphenyl)urea (53 mg, 0.28 mmol), cesium carbonate (92 mg, 0.28 mmol) and epibromohydrine (49 mg, 0.36 mmol) in dry DMF (0.6 mL) was stirred at room temperature for 24 hours. The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with water three times, dried and concentrated to a solid residue. This crude product was recrystallized (ethyl ether and heptane to afford the subtitle compound (18 mg, 26.5%). The mixture was then partitioned between ethyl acetate and water The organic phase was washed with water three times dried concentrated to a solid residue This crude product was recrystallized (ethyl ether and heptane