furan-2-sulfonyl chloride

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:

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: Twenty-three g of 2-furansulfonyl chloride (138 mm) was added dropwise into 200 ml of conc. NH4OH at 0°-5°. After stirring overnight at room temperature, the water was removed under vacuum and the precipitate washed with ice water and dried. Yield: 14 g 2-furansulfonamide m.p. 120-122°. (literature m.p. 120°-122°: JOC 18, 894 (1953)). IR (Nujol) 3250 cm-1, 3100 cm-1, 1600 cm-1 (W), 1550 cm-1, 1310 cm-1, 1190 cm-1, 1140 cm-1 1120 cm-1, 1055 cm-1, 1005 cm-1, 930 cm-1, 880 cm-1, 843 cm-1 (S). the water was removed under vacuum the precipitate washed with ice water dried

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

実験手順: Ninety ml of water, 410 ml of conc. HCl, and 68.0 g of lithium 2-furansulfinate were stirred and cooled to 10°-15°. Liquid chlorine (12.3 ml, 39.4 g) was added dropwise over a 30-minute period. The mixture was stirred an additional 30 minutes at 5°, poured onto ice and extracted with methylene chloride. Evaporation of the methylene chloride yielded 44 g 2-furansulfonyl chloride, b.p. 95° at 7 mm Hg; cooled to 10°-15° poured onto ice extracted with methylene chloride Evaporation of the methylene chloride

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Furansulfonyl chloride (1.01 g, 8.69 mmol) was added dropwise (5 mmol) in CH2Cl2 (20 mL) and triethylamine (2.42 mL, 17.38 mmol). The solution was allowed to warm to 25° C. overnight (19 h). An aliquot was taken and TLC (1:1 EtOAc-hexane) indicated that reaction was complete. It was diluted with CH2Cl2 (100 mL) and the organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated to obtain a crude black oil (0.65 g). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluent: starting with 1:3 EtOAc-hexane and ending with 1:2 EtOAc-hexane to furnish N-[(1S,2S)-1-(hydroxymethyl)-2-methylbutyl]-2-furansulfonamide as an amorphous white solid (0.155 g, 72.12%). Mass Spectrum (−ESI): 246 (M−H)−. Anal. Calc'd for C10H17ClNO4S: C, 48.57; H, 6.93; N, 5.66. Found: C, 48.72; H, 6.78; N, 5.39. the organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL) The organic layer was dried over MgSO4 filtered concentrated to obtain a crude black oil (0.65 g) The crude product was purified by column chromatography, silica gel 230-400 mesh, eluent

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

実験手順: Phosphorus pentachloride (15.29 g, 73.44 mmol) was added portionwise (caution, foaming) over 5 min at 0° C. to chlorosulfonic acid (21.39 g, 183.6 mmol) and the resulting solution was stirred at 0° C. for 10 min. Then, furan (5.0 g, 73.44 mmol) was added in one portion and the resulting dark suspension was stirred at 0° C. for 15 min during which time foaming occurred and subsided. The reaction mixture was then poured onto ice and the resulting suspension was extracted with CH2Cl2 (150 mL). The organic extract was filtered through a pad of celite, washed with brine and dried over MgSO4. The solvent was removed in vacuo to provide 2-furansulfonyl chloride as a black oil (1.01 g, 7.9%). 1H-NMR (DMSO-d6, 400 MHz) δ7.4 (d, 1H); 6.38 (d, 1H); 6.35 (d, 1H). the resulting dark suspension was stirred at 0° C. for 15 min during which time The reaction mixture was then poured onto ice the resulting suspension was extracted with CH2Cl2 (150 mL) The organic extract was filtered through a pad of celite washed with brine dried over MgSO4 The solvent was removed in vacuo

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

実験手順: Following General Procedure B, the title compound (215 mg, 47%) was prepared from 5-chloro-2-methylsulfanyl-phenylamine (260 mg, 1.50 mmol) and furan-2-sulfonyl chloride (250 mg, 1.50 mmol).

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: According to the general procedure B, 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine was reacted with furan-2-sulfonyl chloride to obtain the title compound. 1H NMR (300 MHz, CDCl3): δ 7.53 (br s, D2O exchangeable, 1H), 7.38 (dd, J=1.8 & 10.5 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.21 (d, J=3.0 Hz, 1H), 6.96 (dd, J=8.7 & 16.5 Hz, 1H), 6.87 (ddd, J=1.8, 5.1 & 9.0 Hz, 1H), 6.53 (dd, J=1.8 & 3.6 Hz, 1H), 6.44 (dt, J=5.1, 8.7 & 13.8 Hz, 1H), 6.22 (br s, D2O exchangeable, 1H).