2,6-dichloro-N-(cyclopropylmethyl)aniline

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 58.4 grams of N-cyclopropylcarbonyl-2,6-dichloroaniline was dissolved in 550 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere in a 2 liter 3-necked flask. The mixture was cooled in an ice bath to 4° C. To this mixture was added 389 ml of 0.9 M-diboronhexahydride in anhydrous tetrahydrofuran over a period of one hour and ten minutes while maintaining a temperature of less than 5° C. After addition was complete, the solution was allowed to warm to room temperature and stirred for one hour. The solution was then heated to reflux and reflux was maintained overnight. The solution was then cooled in an ice bath and 225 ml 6 N aqueous hydrogen chloride was added. This mixture was then evaporated in vacuo to remove the tetrahydrofuran. The resultant liquid and solid residue was diluted with 500 ml of water and cooled in an ice bath. 75 g of sodium hydroxide in 300 ml of water was then added. The mixture was then extracted with ether and the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution and dried over sodium sulfate. The resultant mixture was then filtered and the filtrate was evaporated in vacuo. The resultant oil was dissolved in 100 ml of methanol and acidified with 250 ml of methanol/hydrogen chloride and then evaporated in vacuo at 35°-40° C. The resultant oil residue was dissolved in 250 ml of isopropanol and a crystalline precipitate formed. The reaction yielded 33.0 g of white solid N-cyclopropyl methyl-2,6-dichloroaniline having a melting point of 149°-158° C. ten minutes while maintaining a temperature of less than 5° C After addition to warm to room temperature The solution was then heated to reflux reflux was maintained overnight The solution was then cooled in an ice bath This mixture was then evaporated in vacuo to remove the tetrahydrofuran The resultant liquid and solid residue was diluted with 500 ml of water cooled in an ice bath 75 g of sodium hydroxide in 300 ml of water was then added The mixture was then extracted with ether the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution dried over sodium sulfate The resultant mixture was then filtered the filtrate was evaporated in vacuo The resultant oil was dissolved in 100 ml of methanol evaporated in vacuo at 35°-40° C The resultant oil residue was dissolved in 250 ml of isopropanol a crystalline precipitate formed

反応条件: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 58.4 grams of N-cyclopropylcarbonyl-2,6-dichloroaniline was dissolved in 550 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere in a 2 liter 3-necked flask. The mixture was cooled in an ice bath to 4° C. To this mixture was added 389 ml of 0.9 M-diboronhexahydride in anhydrous tetrahydrofuran over a period of one hour and ten minutes while maintaining a temperature of less than 5° C. After addition was complete, the solution was allowed to warm to room temperature and stirred for one hour. The solution was then heated to reflux and reflux was maintained overnight. The solution was then cooled in an ice bath and 225 ml 6 N aqueous hydrogen chloride was added. This mixture was then evaporated in vacuo to remove the tetrahydrofuran. The resultant liquid and solid residue was diluted with 500 ml of water and cooled in an ice bath. 75 g of sodium hydroxide in 300 ml of water was then added. The mixture was then extracted with ether and the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution and dried over sodium sulfate. The resultant mixture was then filtered and the filtrate was evaporated in vacuo. The resultant oil was dissolved in 100 ml of methanol and acidified with 250 ml of methanol/hydrogen chloride and then evaporated in vacuo at 35°-40° C. The resultant oil residue was dissolved in 250 ml of isopropanol and a crystalline precipitate formed. The reaction yielded 33.0 g of white solid N-cyclopropyl methyl-2,6-dichloroaniline having a melting point of 149°-158° C. ten minutes while maintaining a temperature of less than 5° C After addition to warm to room temperature The solution was then heated to reflux reflux was maintained overnight The solution was then cooled in an ice bath This mixture was then evaporated in vacuo to remove the tetrahydrofuran The resultant liquid and solid residue was diluted with 500 ml of water cooled in an ice bath 75 g of sodium hydroxide in 300 ml of water was then added The mixture was then extracted with ether the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution dried over sodium sulfate The resultant mixture was then filtered the filtrate was evaporated in vacuo The resultant oil was dissolved in 100 ml of methanol evaporated in vacuo at 35°-40° C The resultant oil residue was dissolved in 250 ml of isopropanol a crystalline precipitate formed

反応条件: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 58.4 grams of N-cyclopropylcarbonyl-2,6-dichloroaniline was dissolved in 550 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere in a 2 liter 3-necked flask. The mixture was cooled in an ice bath to 4° C. To this mixture was added 389 ml of 0.9 M-diboronhexahydride in anhydrous tetrahydrofuran over a period of one hour and ten minutes while maintaining a temperature of less than 5° C. After addition was complete, the solution was allowed to warm to room temperature and stirred for one hour. The solution was then heated to reflux and reflux was maintained overnight. The solution was then cooled in an ice bath and 225 ml 6 N aqueous hydrogen chloride was added. This mixture was then evaporated in vacuo to remove the tetrahydrofuran. The resultant liquid and solid residue was diluted with 500 ml of water and cooled in an ice bath. 75 g of sodium hydroxide in 300 ml of water was then added. The mixture was then extracted with ether and the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution and dried over sodium sulfate. The resultant mixture was then filtered and the filtrate was evaporated in vacuo. The resultant oil was dissolved in 100 ml of methanol and acidified with 250 ml of methanol/hydrogen chloride and then evaporated in vacuo at 35°-40° C. The resultant oil residue was dissolved in 250 ml of isopropanol and a crystalline precipitate formed. The reaction yielded 33.0 g of white solid N-cyclopropyl methyl-2,6-dichloroaniline having a melting point of 149°-158° C. ten minutes while maintaining a temperature of less than 5° C After addition to warm to room temperature The solution was then heated to reflux reflux was maintained overnight The solution was then cooled in an ice bath This mixture was then evaporated in vacuo to remove the tetrahydrofuran The resultant liquid and solid residue was diluted with 500 ml of water cooled in an ice bath 75 g of sodium hydroxide in 300 ml of water was then added The mixture was then extracted with ether the ether extract was washed twice with 500 ml of water, 250 ml of saturated saline solution dried over sodium sulfate The resultant mixture was then filtered the filtrate was evaporated in vacuo The resultant oil was dissolved in 100 ml of methanol evaporated in vacuo at 35°-40° C The resultant oil residue was dissolved in 250 ml of isopropanol a crystalline precipitate formed