butane-1-sulfonic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from butane-1-sulfonic acid ]4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 228) and 5-(3-amino-(2S)-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one (which was obtained in Example 12) according to the procedure of Example 278 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.82 (t, J=7.3 Hz, 3H), 1.20-1.40 (m, 4H), 1.50-1.70 (m, 2H), 1.80-1.95 (m, 2H), 2.39 (t, J=7.3 Hz, 2H), 2.50-2.80 (m, 5H), 2.85 (t, J=7.3 Hz, 2H), 2.85-3.00 (m, 2H), 3.45-3.60 (m, 2H), 3.75-3.85 (m, 3H), 6.44 (d, J=8.7 Hz, 1H), 6.60 (d, J=8.7 Hz, 1H), 6.89 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 8.74 (s, 1H); MS (ES) m/z: 546.9 (MH+); HRMS Calcd. for C27H39N4O6S(MH+): 547.2590. Found: 547.2583.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from butane-1-sulfonic acid ]4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 228) and 5-(3-amino-(2S)-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one (which was obtained in Example 12) according to the procedure of Example 278 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.82 (t, J=7.3 Hz, 3H), 1.20-1.40 (m, 4H), 1.50-1.70 (m, 2H), 1.80-1.95 (m, 2H), 2.39 (t, J=7.3 Hz, 2H), 2.50-2.80 (m, 5H), 2.85 (t, J=7.3 Hz, 2H), 2.85-3.00 (m, 2H), 3.45-3.60 (m, 2H), 3.75-3.85 (m, 3H), 6.44 (d, J=8.7 Hz, 1H), 6.60 (d, J=8.7 Hz, 1H), 6.89 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 8.74 (s, 1H); MS (ES) m/z: 546.9 (MH+); HRMS Calcd. for C27H39N4O6S(MH+): 547.2590. Found: 547.2583.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.429 g (0.018 moles) of dry dimethyl sulfoxide and 2.27 g (0.015 moles) of dry n-butanesulfonic acid in 13 ml of dry chloroform, was added 2.2110 g (0.0148 moles) of o-methoxyphenyl isocyanate. After thirty minutes at room temperature, the reaction mixture was refluxed for three and a half hours. After cooling to room temperature, the reaction mixture was poured into 180 ml of ice-cold 10% aqueous sodium hydroxide solution. After extracting with methylene chloride, the organic layer was dried over anhydrous sodium carbonate, filtered and 0.10 g of succinimide was added. The resulting solution was concentrated to 100 ml and then refluxed for twenty hours. This solution was cooled, extracted with 10% aqueous sodium hydroxide solution and the organic layer dried over anhydrous magnesium sulfate and filtered. At this point, tridecane was added as an internal standard and the solution was analyzed by gas chromatography. In this manner, there was obtained 0.338 g (22.4%) of o-methoxyaniline and 1.8319 g (67.6%) of 2 -methoxy-6-(methylthiomethyl)aniline. The results are included in Table II. After thirty minutes at room temperature the reaction mixture was refluxed for three and a half hours After extracting with methylene chloride the organic layer was dried over anhydrous sodium carbonate filtered 0.10 g of succinimide was added The resulting solution was concentrated to 100 ml refluxed for twenty hours This solution was cooled extracted with 10% aqueous sodium hydroxide solution the organic layer dried over anhydrous magnesium sulfate filtered At this point, tridecane was added as an internal standard

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.429 g (0.018 moles) of dry dimethyl sulfoxide and 2.27 g (0.015 moles) of dry n-butanesulfonic acid in 13 ml of dry chloroform, was added 2.2110 g (0.0148 moles) of o-methoxyphenyl isocyanate. After thirty minutes at room temperature, the reaction mixture was refluxed for three and a half hours. After cooling to room temperature, the reaction mixture was poured into 180 ml of ice-cold 10% aqueous sodium hydroxide solution. After extracting with methylene chloride, the organic layer was dried over anhydrous sodium carbonate, filtered and 0.10 g of succinimide was added. The resulting solution was concentrated to 100 ml and then refluxed for twenty hours. This solution was cooled, extracted with 10% aqueous sodium hydroxide solution and the organic layer dried over anhydrous magnesium sulfate and filtered. At this point, tridecane was added as an internal standard and the solution was analyzed by gas chromatography. In this manner, there was obtained 0.338 g (22.4%) of o-methoxyaniline and 1.8319 g (67.6%) of 2 -methoxy-6-(methylthiomethyl)aniline. The results are included in Table II. After thirty minutes at room temperature the reaction mixture was refluxed for three and a half hours After extracting with methylene chloride the organic layer was dried over anhydrous sodium carbonate filtered 0.10 g of succinimide was added The resulting solution was concentrated to 100 ml refluxed for twenty hours This solution was cooled extracted with 10% aqueous sodium hydroxide solution the organic layer dried over anhydrous magnesium sulfate filtered At this point, tridecane was added as an internal standard

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After 1-butanesulfonic acid (10 g, 0.072 mol) was dissolved in methylene chloride (50 mL), pyridine (11 g, 0.14 mol) was added dropwise thereto, and the mixture was reacted at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under the reduced pressure to dryness to obtain a crude product containing pyridinium 1-butanesulfonate salt. To a suspension of this crude product (5 g, 0.023 mol) in cyclohexane (50 mL), dimethyl sulfate (15 g, 0.12 mol) was added, and the mixture was reacted at 80° C. for 2 hours. The resultant reaction liquid was condensed under the reduced pressure to obtain the desired product of methyl 1-butanesulfonate. Quantitative analysis by 1H-NMR showed a conversion rate of 77%. the mixture was reacted at room temperature for 2 hours After completion of the reaction the solvent was evaporated under the reduced pressure to dryness to obtain a crude product was added the mixture was reacted at 80° C. for 2 hours The resultant reaction liquid condensed under the reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After 1-butanesulfonic acid (10 g, 0.072 mol) was dissolved in methylene chloride (50 mL), pyridine (11 g, 0.14 mol) was added dropwise thereto, and the mixture was reacted at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under the reduced pressure to dryness to obtain a crude product containing pyridinium 1-butanesulfonate salt. To a suspension of this crude product (5 g, 0.023 mol) in cyclohexane (50 mL), dimethyl sulfate (15 g, 0.12 mol) was added, and the mixture was reacted at 80° C. for 2 hours. The resultant reaction liquid was condensed under the reduced pressure to obtain the desired product of methyl 1-butanesulfonate. Quantitative analysis by 1H-NMR showed a conversion rate of 77%. the mixture was reacted at room temperature for 2 hours After completion of the reaction the solvent was evaporated under the reduced pressure to dryness to obtain a crude product was added the mixture was reacted at 80° C. for 2 hours The resultant reaction liquid condensed under the reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After 1-butanesulfonic acid (10 g, 0.072 mol) was dissolved in methylene chloride (50 mL), pyridine (11 g, 0.14 mol) was added dropwise thereto, and the mixture was reacted at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under the reduced pressure to dryness to obtain a crude product containing pyridinium 1-butanesulfonate salt. To a suspension of this crude product (5 g, 0.023 mol) in cyclohexane (50 mL), dimethyl sulfate (15 g, 0.12 mol) was added, and the mixture was reacted at 80° C. for 2 hours. The resultant reaction liquid was condensed under the reduced pressure to obtain the desired product of methyl 1-butanesulfonate. Quantitative analysis by 1H-NMR showed a conversion rate of 77%. the mixture was reacted at room temperature for 2 hours After completion of the reaction the solvent was evaporated under the reduced pressure to dryness to obtain a crude product was added the mixture was reacted at 80° C. for 2 hours The resultant reaction liquid condensed under the reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a Gotte foam beater (DIN 53 902, Part 1), methane, ethane, propane, butane, n-hexane and n-octane sulfonic acid were tested for their foaming behavior in 0.5% aqueous solution (0° Gh) at 40° C. The solutions of methane, ethane, propane and butane sulfonic acid did not produce any foam.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following a procedure analogous to that of Example 1, butane-1-sulphonic acid and desferrioxamine-B are reacted to give the butane-1-sulphonate salt of desferrioxamine-B. Mp 134° C. C29H58O11 N6S Calcd. C: 49.84%, H: 8.36%, N:12.03%, S:4.59%; Found C:49.52%, H:8.19%, N:12.00%, S:4.14%. are reacted

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 36 g of methanol was dissolved 3.3 g (0.009 mol) of (4-tert-butoxyphenyl)diphenylsulfonium chloride. 1.7 g (0.0063 mol) of lead carbonate and 1.4 g (0.010 mol) of butanesulfonic acid were added to the solution, which was heated at 40° C. After cooling, the precipitate was filtered off and the filtrate was evaporated. 100 g of chloroform was added to the residue, the solution was washed with 100 g of water, and the solvent layer was evaporated again, obtaining 3.5 g (two-steps yield 64%) of (4-tert-butoxyphenyl)diphenylsulfonium butanesulfonate with 97% purity. After cooling the precipitate was filtered off the filtrate was evaporated 100 g of chloroform was added to the residue the solution was washed with 100 g of water the solvent layer was evaporated again