2-chloroethanesulfonyl fluoride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Ethylaniline (48.4 g 0.4 m), triethylamine (40.4 g 0.4 m) and benzene (100 ml) are stirred together at room temperature and 2-chloroethanesulfonyl fluoride (58.6 g, 0.4 m) is added dropwise. The reaction mixture is heated at reflux for 1.5 hr. after the addition is completed. The reaction mixture is cooled and filtered to remove any insoluble salts, and the benzene is removed by distillation. The crude product is drowned into hexane (150 ml) and purified by filtration and washing with hexane. The product melts at 48°-50° C. The reaction mixture is heated at reflux for 1.5 hr after the addition The reaction mixture is cooled filtered to remove any insoluble salts the benzene is removed by distillation purified by filtration washing with hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g, 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45° C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154°-155° C. to rise to 45° C The reaction mixture is then heated at reflux for 3 hrs reaction to cool The product is collected by filtration washed with water and melts at 154°-155° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g, 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45° C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154°-155° C. to rise to 45° C The reaction mixture is then heated at reflux for 3 hrs reaction to cool The product is collected by filtration washed with water and melts at 154°-155° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Ethylaniline (48.4 g 0.4 m), triethylamine (40.4 g 0.4 m) and benzene (100 ml) are stirred together at room temperature and 2-chloroethanesulfonyl fluoride (58.6 g, 0.4 m) is added dropwise. The reaction mixture is heated at reflux for 1.5 hr. after the addition is completed. The reaction mixture is cooled and filtered to remove any insoluble salts, and the benzene is removed by distillation. The crude product is drowned into hexane (150 ml) and purified by filtration and washing with hexane. The product melts at 48°-50° C. The reaction mixture is heated at reflux for 1.5 hr after the addition The reaction mixture is cooled filtered to remove any insoluble salts the benzene is removed by distillation purified by filtration washing with hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Ethylaniline (48.4 g 0.4 m), triethylamine (40.4 g 0.4 m) and benzene (100 ml) are stirred together at room temperature and 2-chloroethanesulfonyl fluoride (58.6 g, 0.4 m) is added dropwise. The reaction mixture is heated at reflux for 1.5 hr. after the addition is completed. The reaction mixture is cooled and filtered to remove any insoluble salts, and the benzene is removed by distillation. The crude product is drowned into hexane (150 ml) and purified by filtration and washing with hexane. The product melts at 48°-50° C. The reaction mixture is heated at reflux for 1.5 hr after the addition The reaction mixture is cooled filtered to remove any insoluble salts the benzene is removed by distillation purified by filtration washing with hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloromethane (126 g), and the organic layers were put together. It was dried over magnesium sulfate, and after filtration, the solvent was distilled off to obtain a crude product (47.1 g). The obtained crude liquid was used for the next step without carrying out purification. under cooling with ice bath while maintaining the internal temperature to be at most 10° C After completion of the dropwise addition, it was stirred at room temperature for 2 hours was added The obtained crude liquid was subjected to liquid separation the obtained aqueous layer was extracted with dichloromethane (124 g) The separated aqueous layer was further extracted with dichloromethane (126 g) It was dried over magnesium sulfate after filtration the solvent was distilled off