Structure of 98-32-8
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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. : | 98-32-8 |
Formula : | C6H8N2O3S |
M.W : | 188.20 |
SMILES Code : | C1=C(C(=CC=C1[S](N)(=O)=O)O)N |
MDL No. : | MFCD00035782 |
Boiling Point : | No data available |
InChI Key : | AVQFHKYAVVQYQO-UHFFFAOYSA-N |
Pubchem ID : | 66814 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
92% | In tetrahydrofuran; at 20℃; for 5h; | To a solution of 3-amino-4-hydroxy-benzenesulfonamide (5.00 g, 26.6 mmol, 1.0 equiv) in anhydrous THF (250 mL) was added slowly thiophosgene (3.67 g, 2.43 mL, 31.9 mmol, 1.2 equiv) via syringe pump over a time period of 1 h. After stirring for 4 h at rt, excess thiophosgene was quenched by addition of a conc. solution of ammonium chloride (100 mL) and the majority of solvent removed by evaporation under reduced pressure. The residue was extracted with ethyl acetate (3.x.100 mL) and the combined organic phases dried over MgSO4 yielding 6.1 g (92percent) of crude product, which was used in the subsequent reaction step without further purification. 1H NMR (300 MHz, DMSO): delta 7.51 (br s, 2H), 7.68 (s, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.78 (d, J=7.7 Hz, 1H), 14.21 (br s, 1H). 13C NMR (75 MHz, DMSO): delta 106.29, 108.47, 120.06, 129.91, 139.54, 148.16, 179.38. MS (ISP): 230.9 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; for 4h;Heating / reflux; | 500 mg of the product of 22A and 400 mg of 2-amino-5-sulfonamido phenol were dissolved in 100 ml THF and refluxed for 4 hours. The obtained crystals were washed with acetone to obtain 225 mg of a product melting at 312° C. Microanalysis theory (percent): C, 40.0; H, 2.64; N, 10.0. obtained (percent): C, 40.0; H, 2.60; N, 9.85. |