Structure of 5284-66-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 5284-66-2 |
| Formula : | C3H8O3S |
| M.W : | 124.16 |
| SMILES Code : | CCCS(=O)(O)=O |
| English Name : | Propane-1-sulfonic acid |
| MDL No. : | MFCD00041889 |
| InChI Key : | KCXFHTAICRTXLI-UHFFFAOYSA-N |
| Pubchem ID : | 78938 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 47% | With hydrogen iodide; dimethyl sulfoxide In water | 1 Example 1 Example 1 n-Propanethiol (0.52 g; 6.8 mmole), dimethyl sulfoxide (0.1 ml; 1.5 mmole), hydrogen iodide (0.02 ml of a 47 wt.% aqueous solution; 0.13 mmole) and water (10 ml) were charged into a glass pressure reactor. The reactor was closed, pressurized with air to about 100 psig, and heated to 110°C. The reactor pressure at this temperature was about 150 psig. The reactor was kept at the same temperature for 24 hours while the contents were stirred, after which time the reactor was cooled and slowly depressurized. The contents of the reactor were extracted with 25 ml of water. In this manner 0.4 g (47% yield) of n-propane sulfonic acid was produced as determined by titration of the aqueous fraction by 0.1 Normal aqueous sodium hydroxide. |
| With nitric acid | ||
| 0.34% | With hydrogen iodide; dimethyl sulfoxide In water | 3 Example 3 Example 3 n-Propanethiol (25.2 g; 330 mmole), dimethyl sulfoxide (5.8 ml; 80 mmole), hydrogen iodide (0.9 ml of a 48 wt.% aqueous solution; 5.7 mmole) and water 4.0 ml (220 mmole) were charged into a glass pressure reactor. The reactor was closed and pressurized with 100 psig air. The reactor was heated to 110°C. The reactor pressure at this temperature was about 150 psig. The reactor was kept at this temperature for 24 hours while stirring the contents with a magnetic stirrer. The reactor was thereafter cooled and slowly depressurized. The contents of the reactor were extracted with 25 ml of water. In this manner 0.14 g (0.34% yield) of the n-propane sulfonic acid was produced as determined by titration of the aqueous fraction by 0.1 Normal aqueous sodium hydroxide. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With phosphorus pentachloride | ||
| With sulfuryl dichloride In N,N-dimethyl-formamide at 100 - 105℃; for 3h; Yield given; | ||
| With triethylamine In acetone at 80℃; for 0.333333h; microwave irradiation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With ammonium sulfite; water | ||
| With ammonium bisulfite; water | ||
| With water; sodium sulfite |
| With water; sodium sulfite | ||
| With sodium sulfite In water for 10h; Heating; Yield given; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | With 3,3-dimethyldioxirane In dichloromethane at -40℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | In ethanol for 24h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | In tetrahydrofuran at 60℃; for 10h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With boron tribromide; potassium iodide In 1,2-dichloro-ethane at 80℃; for 16h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 77% | With Lewatit SP 120 H form In dichloromethane for 4h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In ethyl acetate; isopropyl alcohol | 14; 16 Example 14 : Preparation of Amorphous Compound [A,] n-propanesulfonic acid salt Compound A (186 mg; see Preparation A above) was dissolved in iso-propanol (1.39 mL) and n-propanesulfonic acid [(1] eq. , 95%, [39] [UL)] was added. Ethyl acetate (5.6 mL) was added and the solvent was evaporated until a dry, amorphous solid was formed.; Compound A (229 mg; see Preparation A above) was dissolved in iso-propanol [ (1.43 ML). N-PROPANESULFONIC ACID WAS ADDED (1 EQ. , 95%, 48 I1L). ETHYL ACETATE] was added (2 mL), and then the solution was seeded with crystalline salt from Example 15 above. Further ethyl acetate was added (5 [ML)] and the slurry was left overnight to crystallize. The crystals were filtered off, washed with ethyl acetate (3 x 0.3 [ML)] and dried under vacuum at [40°C.] |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With dihydrogen peroxide; methyltrioxorhenium(VII) In acetonitrile at 20℃; for 0.0166667h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | With (methoxymethylidene)dimethylammonium methyl sulfate; triethylamine In tetrahydrofuran at 20℃; for 4.5h; diastereoselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With (methoxymethylidene)dimethylammonium methyl sulfate; triethylamine In tetrahydrofuran at 20℃; for 5h; diastereoselective reaction; | |
| 73% | With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; triethylamine In dichloromethane at 20℃; | General procedure General procedure: Phosphonitrilic chloride (3) (0.5 mmol) was added to a solution of the sulfonic acid (1.5 mmol), the imine (1.0 mmol) and Et3N (5.0 mmol) in dry CH2Cl2 (15 ml) at room temperature and the mixture was stirred for 8-10 h. The mixture was washed successively with saturated NaHCO3 (15 ml) and brine (15 ml). The organic layer was dried (Na2SO4), filtered and the solvent was removed to give the crude product. Pure b-sultams 6a-n were obtained by purification via short column chromatography on silica-gel (EtOAc/hexane, 3:7). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; Green chemistry; stereoselective reaction; | General procedure for the synthesis of β-sultams 3a-l. General procedure: The T3P (1.5 mmol, 50% solution in DMF) was added to a solution of sulfonic acid (1.5 mmol), imine (1 mmol) and triethylamine (5.0 mmol) in dry CH2Cl2 (20 ml) at 0 °C and the mixture was stirred overnight at room temperature. The reaction mixture was washed successively with saturated NaHCO3 (20 ml) and brine (20 ml). The organic layer was dried (Na2SO4), filtered and the solvent was removed to give the crude product, which was purified by short column chromatography on silica gel (EtOAc-hexane, 3 : 7) to give pure β-sultams 3a-l. Spectral data for known compounds 3b and 3d-l have been previously reported. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | In acetone for 12h; Reflux; | 1 Preparation Example 1: Propane sulfonic acid internal salt To a 100 mL round bottom flask was added 4-methylpyridine (0.01 mol), l, 3-propanesultone (O.Olmol) and50 mL of acetone, heated to reflux for 12 hours. After cooling, the solid was precipitated and filtered under reduced pressure to give 2.1 g of a white solid in 91% yield. |