Structure of MTSEA HBr
CAS No.: 16599-33-0
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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.
Synonyms: MTSEA hydrobromide; MTSEA; Methanethiosulfonate Ethylammonium
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| CAS No. : | 16599-33-0 |
| Formula : | C3H10BrNO2S2 |
| M.W : | 236.15 |
| SMILES Code : | CS(=O)(SCCN)=O.[H]Br |
| Synonyms : |
MTSEA hydrobromide; MTSEA; Methanethiosulfonate Ethylammonium
|
| English Name : | S-(2-Aminoethyl) methanesulfonothioate hydrobromide |
| MDL No. : | MFCD00269887 |
* 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 |
|---|---|---|
| 90 mg | With benzotriazol-1-ol; triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 22h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | In DMF (N,N-dimethyl-formamide) at 70℃; for 4h; | 1.B The schematic presentation of the synthesis of a light sensitive compounds is given in Figure 6. In the first reaction sodium methanethiosulfonate (1.47g, 11 mmol) was added to the solution of 2-bromoethylamine hydrobromide (1) (2.05g, 10 mmol) in DMF (5 ml) and mixture was heated at 70°C for 4 hours, solid precipitate was filtered out and DMF was evaporated in vacuo. The residue was dissolved in a small amount of boiling acetonitrile (20 ml), filtered and the filtrate evaporated in vacuo. The recrystallization from acetonitrile-ether gave product. In the second reaction, 236 mg, 1 mmol of methanethiosulfonic acid S- (2-amino-ethyl) ester hydrobromide (2) was dissolved in 3 ml of DMF and 6-nitroveratrylchlorofotmate (303 mg, 1.1 mmol) and pyridine (0.5 ml) were added. After overnight stirring, the mixture was poured into water (10 ml) and extracted with dichloromethane (3x 30 ml). All the solvents were evaporated in vacuo and product, methanethiosulfonic acid S-[2-(4,5-dimethoxy-2-nitrobenzyloxycarbonylamino)-ethyl] ester (3), chromatographed on Si-gel using dichloromethane as an eluent.Results and Discussion The yield of the first reaction was 85%., that of the second reaction was 48%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 48% | With pyridine In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; | 1.B The schematic presentation of the synthesis of a light sensitive compounds is given in Figure 6. In the first reaction sodium methanethiosulfonate (1.47g, 11 mmol) was added to the solution of 2-bromoethylamine hydrobromide (1) (2.05g, 10 mmol) in DMF (5 ml) and mixture was heated at 70°C for 4 hours, solid precipitate was filtered out and DMF was evaporated in vacuo. The residue was dissolved in a small amount of boiling acetonitrile (20 ml), filtered and the filtrate evaporated in vacuo. The recrystallization from acetonitrile-ether gave product. In the second reaction, 236 mg, 1 mmol of methanethiosulfonic acid S- (2-amino-ethyl) ester hydrobromide (2) was dissolved in 3 ml of DMF and 6-nitroveratrylchlorofotmate (303 mg, 1.1 mmol) and pyridine (0.5 ml) were added. After overnight stirring, the mixture was poured into water (10 ml) and extracted with dichloromethane (3x 30 ml). All the solvents were evaporated in vacuo and product, methanethiosulfonic acid S-[2-(4,5-dimethoxy-2-nitrobenzyloxycarbonylamino)-ethyl] ester (3), chromatographed on Si-gel using dichloromethane as an eluent.Results and Discussion The yield of the first reaction was 85%., that of the second reaction was 48%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 39% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3.5h; | 8.2 8.2 8.2 Preparation of 1-(2,6-dimethylphenyl)-2,8,8-trioxo-1,4-diaza-7,8-dithianonane A solution of 2-bromo-N-(2,6-dimethylphenyl)acetamide (2 g; 8.26 mmol), aminoethyl methanethiosulfonate hydrobromide (2.8 g; 11.86 mmol), and diisopropylethylamine (4 mL; 23 mmol) in dry DMF (70 mL) was stirred at room temperature for 3.5 hours. The solution was evaporated and the residue purified by column chromatography on SiO2. The column was eluted with CH2Cl2/MeOH/NH4OH 95:5:0.2 and evaporation of the fractions containing the desired product afforded a pale yellow oil (1.66 g) which crystallized upon standing in the freezer. This was dissolved in methanol/ether (1:1; 50 mL). A saturated solution of HCl in ether (4 mL) was added. The precipitated hydrochloride salt was filtered and dried to yield a light brown solid (1.15 g; 39% yield) with a melting point of 158-162°C. 1H NMR (500 MHz, (CD3)2SO) δ 9.93 (s, 1H), 9.32 (s, br, 2H), 7.10-7.07 (m, 3H); 4.08 (s, 2H), 3.61 (s, 3H), 3.54 (t, J=7.2 Hz, 2H), 3.40 (t, J=7.2 Hz, 2H), 2.16 (s, 6H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With diisopropylamine In N,N-dimethyl-formamide | 13 Example 13: Example 13: Carbohydrate-Based Methanethiosulfonate (MTS) Reagents The following is an example of how a general class of carbohydrate-based MTS reagents are formed from the well known glycosyl cyanates. The carbohydrates can be nonsaccharides. Similar chemistry using glycosyl thiocyanates affords the corresponding thioderivatives. The isocyanate above (1.5g; 4.02 mmol) was dissolved in 50mL of dry DMF. Aminoethyl methanethiosulfonate hydrobromide (0.95 g; 4.02 mmol) was added followed by diisopropylamine (0.784 mL; 4.5 mmol). The solvent was evaporated. The residue was applied to a column of silica gel, which was eluted with chloroform:methanol (95:5). The fractions containing product were combined and evaporated to dryness to give the tetraacetate product as a viscous yellow oil of 2.25 g (4.2 mmol). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 63% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1.6 g | With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 30h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In methanol; acetonitrile | 2.3 3. 3. S-(2-Aminoethyl) Methanethiosulfonate Hydrobromide 2 grams of sodium methanethiosulfonate from Step 2 above (15 mmol) and 2 grams of 2-bromoethylamine hydrobromide (10 mmol) were dissolved in 50 ml of methanol. The resulting solution was then refluxed for 3 hours, and it was concentrated in vacuo to dry. The residue was suspended in 30 ml of acetonitrile, and the precipitates were filtered off. The filtrate was concentrated in vacuo to form a yellow sticky oil. To the residue, was added a mixture of acetonitrile and diethylether (2.5 ml/2.5 ml) and the mixture was stirred vigorously overnight to give a yellow pasty solid. The remaining liquid was poured off and the solid was suspended in above solvent mixture (2.5 ml/2.5 ml) and triturated. The mixture was filtered, and the solid was washed with the above solvent mixture, and ether to give an off-white solid, and dried in vacuum with P2O5 to give 1.45 gram powder. 1H NMR (300 MHz, D2O)H 3.497 (5H, m), 3.371 (2H, t, J=17), 4.240 (2H, br) 13C NMR (300 MHz, D2O)C 50.994 (CH3), 41.016 (CH2), 34.149 (CH2) IR: 1309.4 cm-1, 1132.0 cm-1 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 40% | With 1-hydroxy-pyrrolidine-2,5-dione; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydroxylamine In methanol; water for 1h; Inert atmosphere; | 3 (0183) Compound 8: (0183) Compound 8: Intermediate 2 (51 mg, 0.132 mmol) was dissolved in 2 mL methanol, 2-(aminoethyl)methanethiosulfonate hydrobromide (36 mg, 0.152 mmol) was added, followed by hydroxylamine (0.02 mL 50% in water, 0.653 mmol). After 1 hr this was purified by reverse phase HPLC to yield Compound 8 as a white solid. ES (+) MS m/e = 423 (M+1). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 4h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 4h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 72% | With potassium carbonate In dichloromethane; water at 0℃; |