2,2,2-trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethanone

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: A solution of 2,2,2-trichloro-1-(4-chloro-1H-Pyrrol-2-yl)ethanone (14.0 g, 56.7 mmol) in THF (100 mL) was bubbled with ammonium gas for 2 h at room temperature. TLC analysis indicated that there was complete conversion of starting material. The reaction mixture was concentrated in vacuo to yield 7.5 g of the above compound (51.88 mmol, yield 92%). 1H-NMR (Acetone-d6) δ 10.92 (br s, 1H), 7.21 (br s, 1H), 7.02 (s, 1H), 6.84 (s, 1H), 6.57 (br s, 1H). The reaction mixture was concentrated in vacuo

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

実験手順: To a solution of 2-(trichloroacetyl)pyrrole (4.0 g, 18.83 mmol) in chloroform (28 ml) at 0° C. was added sulfuryl chloride (13 mL, 13.2 mmol). The mixture was stirred for 17 hours at room temperature. TLC analysis indicated 50% conversion of starting material. Sulfuryl chloride (13 mL, 13.2 mmol) was added and the reaction mixture was stirred for another 4 hours at room temperature. The reaction was quenched with distilled water (50 mL). CH2Cl2 (50 mL) was added to the reaction and the solution was transferred to a separatory funnel and the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×50 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated in vacuo to yield 3.5 g of the above compound (14.18 mmol, yield 75%). 1H-NMR (CDCl3-d1) δ 9.45 (s, 1H), 7.27 (dd, J=2.8, 1.6, 1H), 7.12 (dd, J=3.2, 1.6 Hz, 1H). the reaction mixture was stirred for another 4 hours at room temperature The reaction was quenched with distilled water (50 mL) CH2Cl2 (50 mL) was added to the reaction the solution was transferred to a separatory funnel the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×50 mL) The combined organic layers were collected dried (MgSO4) filtered concentrated in vacuo

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

実験手順: To a solution of 2-(trichloroacetyl)pyrrole (4.0 g, 18.83 mmol) in chloroform (28 ml) at 0° C. was added sulfuryl chloride (13 mL, 13.2 mmol). The mixture was stirred for 17 hours at room temperature. TLC analysis indicated 50% conversion of starting material. Sulfuryl chloride (13 mL, 13.2 mmol) was added and the reaction mixture was stirred for another 4 hours at room temperature. The reaction was quenched with distilled water (50 mL). CH2Cl2 (50 mL) was added to the reaction and the solution was transferred to a separatory funnel and the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×50 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated in vacuo to yield 3.5 g of the above compound (14.18 mmol, yield 75%). 1H-NMR (CDCl3-d1) δ 9.45 (s, 1H), 7.27 (dd, J=2.8, 1.6, 1H), 7.12 (dd, J=3.2, 1.6 Hz, 1H). the reaction mixture was stirred for another 4 hours at room temperature The reaction was quenched with distilled water (50 mL) CH2Cl2 (50 mL) was added to the reaction the solution was transferred to a separatory funnel the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×50 mL) The combined organic layers were collected dried (MgSO4) filtered concentrated in vacuo

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: A solution of 2,2,2-trichloro-1-(4-chloro-1H-Pyrrol-2-yl)ethanone (14.0 g, 56.7 mmol) in THF (100 mL) was bubbled with ammonium gas for 2 h at room temperature. TLC analysis indicated that there was complete conversion of starting material. The reaction mixture was concentrated in vacuo to yield 7.5 g of the above compound (51.88 mmol, yield 92%). 1H-NMR (Acetone-d6) δ 10.92 (br s, 1H), 7.21 (br s, 1H), 7.02 (s, 1H), 6.84 (s, 1H), 6.57 (br s, 1H). The reaction mixture was concentrated in vacuo

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

実験手順: To a solution of 2-(trichloroacetyl)pyrrole (4.0 g, 18.83 mmol) in chloroform (28 ml) at 0° C. was added sulfuryl chloride (13 mL, 13.2 mmol). The mixture was stirred for 17 hours at room temperature. TLC analysis indicated 50% conversion of starting material. Sulfuryl chloride (13 mL, 13.2 mmol) was added and the reaction mixture was stirred for another 4 hours at room temperature. The reaction was quenched with distilled water (50 mL). CH2Cl2 (50 mL) was added to the reaction and the solution was transferred to a separatory funnel and the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×50 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated in vacuo to yield 3.5 g of the above compound (14.18 mmol, yield 75%). 1H-NMR (CDCl3-d1) δ 9.45 (s, 1H), 7.27 (dd, J=2.8, 1.6, 1H), 7.12 (dd, J=3.2, 1.6 Hz, 1H). the reaction mixture was stirred for another 4 hours at room temperature The reaction was quenched with distilled water (50 mL) CH2Cl2 (50 mL) was added to the reaction the solution was transferred to a separatory funnel the organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×50 mL) The combined organic layers were collected dried (MgSO4) filtered concentrated in vacuo

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

実験手順: To a solution of 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone (1 eq.) in dry DCM (1 M) at 0° C. was added sulfuryl chloride (1.15 eq.) dropwise. The mixture was stirred overnight at RT, washed with water (2×) and sat. aq. NaHCO3 solution. The organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by on chromatography on silica gel, eluting with petroleum ether/Et2O to afford the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ: 9.45 (1H, br. S), 7.26 (1H, s), 7.09 (1H, s). washed with water (2×) and sat. aq. NaHCO3 solution The organic phase was separated dried (Na2SO4) concentrated under reduced pressure The crude product was purified by on chromatography on silica gel eluting with petroleum ether/Et2O