P-癸烷氧基苯胺

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

实验步骤: Next, acetic acid (100 ml) was added to the 4-decyloxyaniline 3 (23.4 g, 93.7 mmol) thus obtained, and potassium thiocyanate (23.5 g, 242 mmol) was then added thereto. The solution was thoroughly cooled in an ice bath, and an acetic acid solution of bromine (5.8 ml/50 ml) was then added dropwise thereto over a period of about 3 hr. After the completion of the dropwise addition of the solution, the mixture was stirred at room temperature for about 2 hr. Thereafter, water (200 ml) was added, and the mixture was refluxed for about 30 min and was then hot-filtered. The filtrate was made alkaline by the addition of aqueous ammonia, and saturated brine was further added thereto. The precipitated solid was collected by filtration to give 2-amino-6-decyloxybenzothiazole 4 (14.22 g, 49.5%) as a light purple solid. The product was purified by column chromatography on silica gel (hexane: AcOEt=1:2). thus obtained The solution was thoroughly cooled in an ice bath After the completion of the dropwise addition of the solution the mixture was refluxed for about 30 min was then hot-filtered by the addition of aqueous ammonia, and saturated brine was further added The precipitated solid was collected by filtration

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

实验步骤: Next, acetic acid (100 ml) was added to the 4-decyloxyaniline 3 (23.4 g, 93.7 mmol) thus obtained, and potassium thiocyanate (23.5 g, 242 mmol) was then added thereto. The solution was thoroughly cooled in an ice bath, and an acetic acid solution of bromine (5.8 ml/50 ml) was then added dropwise thereto over a period of about 3 hr. After the completion of the dropwise addition of the solution, the mixture was stirred at room temperature for about 2 hr. Thereafter, water (200 ml) was added, and the mixture was refluxed for about 30 min and was then hot-filtered. The filtrate was made alkaline by the addition of aqueous ammonia, and saturated brine was further added thereto. The precipitated solid was collected by filtration to give 2-amino-6-decyloxybenzothiazole 4 (14.22 g, 49.5%) as a light purple solid. The product was purified by column chromatography on silica gel (hexane: AcOEt=1:2). thus obtained The solution was thoroughly cooled in an ice bath After the completion of the dropwise addition of the solution the mixture was refluxed for about 30 min was then hot-filtered by the addition of aqueous ammonia, and saturated brine was further added The precipitated solid was collected by filtration

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

实验步骤: Ethanol (100 ml) and concentrated hydrochloric acid (5 ml) were added to the 4-decyloxynitrobenzene 2 (28.3 g, 101 mmol) thus obtained to prepare a solution which was then cooled in an ice bath. A hydrochloric acid solution of tin(II) chloride dihydrate (101.3 g, 450 mmol/HCl 50 ml) was added thereto. The mixture was stirred at room temperature for about 2 hr and was then stirred with heating at 60° C. for about 30 min. After the completion of the reaction, the resultant precipitate was collected by filtration. A 3 N aqueous sodium hydroxide solution was added to the collected precipitate, followed by extraction with ether. The filtrate was concentrated, and a 3 N aqueous sodium hydroxide solution was then added to the concentrate. The mixture was extracted with ether. The extract was washed with water, was then dried over sodium sulfate, and was concentrated to give 4-decyloxyaniline 3 as a reddish orange liquid (23.4 g, 92.7%). thus obtained to prepare a solution which was then cooled in an ice bath was then stirred with heating at 60° C. for about 30 min After the completion of the reaction the resultant precipitate was collected by filtration A 3 N aqueous sodium hydroxide solution was added to the collected precipitate followed by extraction with ether The filtrate was concentrated a 3 N aqueous sodium hydroxide solution was then added to the concentrate The mixture was extracted with ether The extract was washed with water was then dried over sodium sulfate was concentrated

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

实验步骤: Next, acetic acid (100 ml) was added to the 4-decyloxyaniline 3 (23.4 g, 93.7 mmol) thus obtained, and potassium thiocyanate (23.5 g, 242 mmol) was then added thereto. The solution was thoroughly cooled in an ice bath, and an acetic acid solution of bromine (5.8 ml/50 ml) was then added dropwise thereto over a period of about 3 hr. After the completion of the dropwise addition of the solution, the mixture was stirred at room temperature for about 2 hr. Thereafter, water (200 ml) was added, and the mixture was refluxed for about 30 min and was then hot-filtered. The filtrate was made alkaline by the addition of aqueous ammonia, and saturated brine was further added thereto. The precipitated solid was collected by filtration to give 2-amino-6-decyloxybenzothiazole 4 (14.22 g, 49.5%) as a light purple solid. The product was purified by column chromatography on silica gel (hexane: AcOEt=1:2). thus obtained The solution was thoroughly cooled in an ice bath After the completion of the dropwise addition of the solution the mixture was refluxed for about 30 min was then hot-filtered by the addition of aqueous ammonia, and saturated brine was further added The precipitated solid was collected by filtration

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

实验步骤: Ethanol (100 ml) and concentrated hydrochloric acid (5 ml) were added to the 4-decyloxynitrobenzene 2 (28.3 g, 101 mmol) thus obtained to prepare a solution which was then cooled in an ice bath. A hydrochloric acid solution of tin(II) chloride dihydrate (101.3 g, 450 mmol/HCl 50 ml) was added thereto. The mixture was stirred at room temperature for about 2 hr and was then stirred with heating at 60° C. for about 30 min. After the completion of the reaction, the resultant precipitate was collected by filtration. A 3 N aqueous sodium hydroxide solution was added to the collected precipitate, followed by extraction with ether. The filtrate was concentrated, and a 3 N aqueous sodium hydroxide solution was then added to the concentrate. The mixture was extracted with ether. The extract was washed with water, was then dried over sodium sulfate, and was concentrated to give 4-decyloxyaniline 3 as a reddish orange liquid (23.4 g, 92.7%). thus obtained to prepare a solution which was then cooled in an ice bath was then stirred with heating at 60° C. for about 30 min After the completion of the reaction the resultant precipitate was collected by filtration A 3 N aqueous sodium hydroxide solution was added to the collected precipitate followed by extraction with ether The filtrate was concentrated a 3 N aqueous sodium hydroxide solution was then added to the concentrate The mixture was extracted with ether The extract was washed with water was then dried over sodium sulfate was concentrated