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Structure of 1593-60-8
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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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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 1593-60-8 |
Formula : | C7H9NO3S |
M.W : | 187.22 |
SMILES Code : | O=S(C1=CC=C(C)C=C1)(NO)=O |
MDL No. : | MFCD11850835 |
InChI Key : | XMJJPCJUQLGGND-UHFFFAOYSA-N |
Pubchem ID : | 10081163 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H315-H319-H228 |
Precautionary Statements: | P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
Class: | 4.1 |
UN#: | 1325 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
87.5% | With hydroxylamine hydrochloride; magnesium oxide; In tetrahydrofuran; methanol; water; at 20℃; | Hydroxylamine hydrochloride (7.2 g, 86 mmol) was dissolved in methanol (30 ml) and water (20 ml), magnesium oxide (5.1 g, 129 mmol) was added, stirred for 10 minutes, then p-toluenesulfonyl chloride (8 g, 43 mmol) in tetrahydrofuran (300 ml), stirred vigorously at room temperature, and reacted to TLC to monitor the starting material for complete reaction. The extract was filtered through Celite, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-hydroxy-4-methylbenzenesulfonamide (7 g, white solid) in 87.5% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With iodine; In dichloromethane; water; at 25℃; for 3h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.400.0971. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With ytterbium(III) triflate; In dichloromethane; at 25℃; for 2h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With iodine; In dichloromethane; water; at 25℃; for 2h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With iodine; In dichloromethane; water; at 25℃; for 4h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With N-Bromosuccinimide; ytterbium(III) triflate; In dichloromethane; at 25℃; for 0.5h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) N-tosyl hydroxylamine 2 (0.5 mmol), and NBS (0.6 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at 25 C for 0.5 h. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With ytterbium(III) triflate; In dichloromethane; at 25℃; for 2h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With iodine; In dichloromethane; water; at 25℃; for 2h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With iodine; In dichloromethane; water; at 25℃; for 4h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With ytterbium(III) triflate; In dichloromethane; at 25℃; for 3h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With iodine; at 25℃; for 4h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With N-Bromosuccinimide; ytterbium(III) triflate; In dichloromethane; at 25℃; for 0.5h; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) N-tosyl hydroxylamine 2 (0.5 mmol), and NBS (0.6 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at 25 C for 0.5 h. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With ytterbium(III) triflate; In dichloromethane; for 3h;Reflux; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in dry DCM (5 mL) was added Yb(OTf)3 (0.05 mmol) slowly at 25 C, and the reaction mixture was stirred at the shown temperature for an indicated period of time shown in text. Saturated aqueous brine was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel with DCM/hexane as eluent to give 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With iodine; In dichloromethane; water; for 12h;Reflux; | General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5. |
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