N-[2-(3-bromophenyl)propan-2-yl]-2-chloroacetamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide (20.3 g) in ethanol (120 mL) was added acetic acid (20 mL). The reaction mixture was stirred at reflux for 18 h. The solution was cooled to room temperature and the precipitate was filtered off on a celite pad. The filtrate was concentrated and the residue was dissolved in EtOAc. The organic layer was treated with aqueous NaOH [1.0M] solution, dried over Na2SO4 and concentrated. The crude material was treated with a solution of HCl/dioxane [4M]. The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether and used as is for the next step (7.50 g, 43%). 1H NMR (400 MHz, CD3OD) δ 7.69 (q, J=1.8 Hz, 1H), 7.55 (ddd, J=1.0, 1.8, 7.9 Hz, 1H), 7.49 (ddd, J=1.0, 2.0, 8.0 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 1.71 (s, 6H) ppm. at reflux for 18 h the precipitate was filtered off on a celite pad The filtrate was concentrated the residue was dissolved in EtOAc The organic layer was treated with aqueous NaOH [1.0M] solution dried over Na2SO4 concentrated The crude material was treated with a solution of HCl/dioxane [4M] The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether

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

実験手順: To a solution of N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide (20.3 g) in ethanol (120 mL) was added acetic acid (20 mL). The reaction mixture was stirred at reflux for 18 h. The solution was cooled to room temperature and the precipitate was filtered off on a celite pad. The filtrate was concentrated and the residue was dissolved in EtOAc. The organic layer was treated with aqueous NaOH [1.0M] solution, dried over Na2SO4 and concentrated. The crude material was treated with a solution of HCl/dioxane [4M]. The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether and used as is for the next step (7.50 g, 43%). 1H NMR (400 MHz, CD3OD) δ 7.69 (q, J=1.8 Hz, 1H), 7.55 (ddd, J=1.0, 1.8, 7.9 Hz, 1H), 7.49 (ddd, J=1.0, 2.0, 8.0 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 1.71 (s, 6H) ppm. at reflux for 18 h the precipitate was filtered off on a celite pad The filtrate was concentrated the residue was dissolved in EtOAc The organic layer was treated with aqueous NaOH [1.0M] solution dried over Na2SO4 concentrated The crude material was treated with a solution of HCl/dioxane [4M] The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether

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

実験手順: To a solution of N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide (20.3 g) in ethanol (120 mL) was added acetic acid (20 mL). The reaction mixture was stirred at reflux for 18 h. The solution was cooled to room temperature and the precipitate was filtered off on a celite pad. The filtrate was concentrated and the residue was dissolved in EtOAc. The organic layer was treated with aqueous NaOH [1.0M] solution, dried over Na2SO4 and concentrated. The crude material was treated with a solution of HCl/dioxane [4M]. The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether and used as is for the next step (7.50 g, 43%). 1H NMR (400 MHz, CD3OD) δ 7.69 (q, J=1.8 Hz, 1H), 7.55 (ddd, J=1.0, 1.8, 7.9 Hz, 1H), 7.49 (ddd, J=1.0, 2.0, 8.0 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 1.71 (s, 6H) ppm. at reflux for 18 h the precipitate was filtered off on a celite pad The filtrate was concentrated the residue was dissolved in EtOAc The organic layer was treated with aqueous NaOH [1.0M] solution dried over Na2SO4 concentrated The crude material was treated with a solution of HCl/dioxane [4M] The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether

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

実験手順: To a solution of N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide (20.3 g) in ethanol (120 mL) was added acetic acid (20 mL). The reaction mixture was stirred at reflux for 18 h. The solution was cooled to room temperature and the precipitate was filtered off on a celite pad. The filtrate was concentrated and the residue was dissolved in EtOAc. The organic layer was treated with aqueous NaOH [1.0M] solution, dried over Na2SO4 and concentrated. The crude material was treated with a solution of HCl/dioxane [4M]. The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether and used as is for the next step (7.50 g, 43%). 1H NMR (400 MHz, CD3OD) δ 7.69 (q, J=1.8 Hz, 1H), 7.55 (ddd, J=1.0, 1.8, 7.9 Hz, 1H), 7.49 (ddd, J=1.0, 2.0, 8.0 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 1.71 (s, 6H) ppm. at reflux for 18 h the precipitate was filtered off on a celite pad The filtrate was concentrated the residue was dissolved in EtOAc The organic layer was treated with aqueous NaOH [1.0M] solution dried over Na2SO4 concentrated The crude material was treated with a solution of HCl/dioxane [4M] The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether

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

実験手順: The mixture of N-[1-(3-bromo-phenyl)-1-methyl-ethyl]-2-chloro-acetamide (1.0 g, 3.5 mmol), thiourea (0.32 g, 4.2 mmol), acetic acid (1.5 mL) in ethanol (7 mL) was heated to reflux for 10 h and brought to room temperature. Water was added to the mixture until a precipitate was formed which was filtered. The filtrate was made basic pH 7-8 with 15% NaOH. The product was extracted with ethyl acetate and concentrated to afford a yellow solid. M+1=214. was heated to reflux for 10 h brought to room temperature was formed which was filtered The product was extracted with ethyl acetate concentrated to afford a yellow solid

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of the 2-(3-bromo-phenyl)-propan-2-ol and (0.76 g, 3.6 mmol) and chloro-acetonitrile (7 mL) was added acetic acid (0.6 mL) and the resulting mixture was cooled to 0° C. Concentrated sulfuric acid (0.6 mL) was added dropwise and the mixture was brought to room temperature and stirred for 17 h. Mixture was poured into ice-water (10 mL) and extracted with ethylacetate. The extracts were combined, dried over magnesium sulfate and concentrated to afford a white solid. M+1=291. was brought to room temperature extracted with ethylacetate dried over magnesium sulfate concentrated to afford a white solid