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Chemical Structure| 1593-60-8 Chemical Structure| 1593-60-8

Structure of 1593-60-8

Chemical Structure| 1593-60-8

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Product Details of [ 1593-60-8 ]

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

Safety of [ 1593-60-8 ]

GHS Pictogram:
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:

Application In Synthesis of [ 1593-60-8 ]

* 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.

  • Downstream synthetic route of [ 1593-60-8 ]

[ 1593-60-8 ] Synthesis Path-Downstream   1~55

  • 1
  • [ 98-59-9 ]
  • [ 1593-60-8 ]
YieldReaction ConditionsOperation 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.
  • 2
  • C26H23NO3S [ No CAS ]
  • [ 1593-60-8 ]
  • 3
  • [ 100-42-5 ]
  • [ 1593-60-8 ]
  • [ 1377813-85-8 ]
  • 4
  • [ 1073-67-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-86-9 ]
  • 5
  • [ 637-69-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-95-0 ]
  • 6
  • [ 826-74-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-99-4 ]
  • 7
  • [ 6380-23-0 ]
  • [ 1593-60-8 ]
  • [ 1377813-97-2 ]
  • 8
  • [ 7315-32-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-98-3 ]
  • 9
  • [ 100-13-0 ]
  • [ 1593-60-8 ]
  • [ 1377813-94-9 ]
  • 10
  • [ 405-99-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-90-5 ]
  • 11
  • [ 2039-82-9 ]
  • [ 1593-60-8 ]
  • [ 1377813-89-2 ]
  • 12
  • [ 3435-51-6 ]
  • [ 1593-60-8 ]
  • [ 1377813-93-8 ]
  • 13
  • [ 402-50-6 ]
  • [ 1593-60-8 ]
  • [ 1377813-92-7 ]
  • 14
  • [ 394-46-7 ]
  • [ 1593-60-8 ]
  • [ 1377813-91-6 ]
  • 15
  • [ 2039-85-2 ]
  • [ 1593-60-8 ]
  • [ 1377813-87-0 ]
  • 16
  • [ 2039-87-4 ]
  • [ 1593-60-8 ]
  • [ 1377813-88-1 ]
  • 17
  • [ 1593-60-8 ]
  • [ 768-03-6 ]
  • [ 1377814-01-1 ]
  • 18
  • [ 1262863-78-4 ]
  • [ 1593-60-8 ]
  • N-hydroxy-4-methyl-N-[3-phenyl-1-(1-tosyl-1H-indol-3-yl)prop-2-ynyl]benzenesulfonamide [ No CAS ]
  • 19
  • [ 1369593-22-5 ]
  • [ 1593-60-8 ]
  • N-hydroxy-N-[1-(4-methoxyphenyl)hex-2-ynyl]-4-methylbenzenesulfonamide [ No CAS ]
  • 20
  • [ 1593-60-8 ]
  • 1-phenylnon-2-yn-1-ol [ No CAS ]
  • N-hydroxy-4-methyl-N-(1-phenylnon-2-ynyl)benzenesulfonamide [ No CAS ]
  • 21
  • [ 1817-49-8 ]
  • [ 1593-60-8 ]
  • [ 1415035-26-5 ]
YieldReaction ConditionsOperation 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.
  • 22
  • [ 1593-60-8 ]
  • [ 73502-43-9 ]
  • [ 1415035-11-8 ]
YieldReaction ConditionsOperation 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.
  • 23
  • [ 5876-69-7 ]
  • [ 1593-60-8 ]
  • [ 1415035-18-5 ]
YieldReaction ConditionsOperation 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.
  • 24
  • [ 1522-13-0 ]
  • [ 1593-60-8 ]
  • [ 1415035-12-9 ]
YieldReaction ConditionsOperation 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.
  • 25
  • [ 1522-13-0 ]
  • [ 1593-60-8 ]
  • [ 1415035-27-6 ]
YieldReaction ConditionsOperation 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.
  • 26
  • [ 1522-13-0 ]
  • [ 1593-60-8 ]
  • [ 1415034-97-7 ]
YieldReaction ConditionsOperation 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.
  • 27
  • [ 1593-60-8 ]
  • [ 548796-81-2 ]
  • [ 1415034-99-9 ]
YieldReaction ConditionsOperation 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.
  • 28
  • [ 1593-60-8 ]
  • [ 548796-81-2 ]
  • [ 1415035-13-0 ]
YieldReaction ConditionsOperation 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.
  • 29
  • [ 1719-18-2 ]
  • [ 1593-60-8 ]
  • [ 1415035-00-5 ]
YieldReaction ConditionsOperation 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.
  • 30
  • [ 1719-18-2 ]
  • [ 1593-60-8 ]
  • [ 1415035-14-1 ]
YieldReaction ConditionsOperation 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.
  • 31
  • [ 1593-60-8 ]
  • [ 408526-00-1 ]
  • [ 1415035-01-6 ]
YieldReaction ConditionsOperation 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.
  • 32
  • [ 1593-60-8 ]
  • [ 408526-00-1 ]
  • [ 1415035-15-2 ]
YieldReaction ConditionsOperation 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.
  • 33
  • [ 1593-60-8 ]
  • [ 408526-00-1 ]
  • [ 1415035-28-7 ]
YieldReaction ConditionsOperation 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.
  • 34
  • [ 62698-34-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-02-7 ]
YieldReaction ConditionsOperation 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.
  • 35
  • [ 62698-34-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-16-3 ]
YieldReaction ConditionsOperation 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.
  • 36
  • [ 62698-34-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-29-8 ]
YieldReaction ConditionsOperation in experiment
53% 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.
  • 37
  • [ 1593-60-8 ]
  • [ 408526-05-6 ]
  • [ 1415035-03-8 ]
YieldReaction ConditionsOperation in experiment
95% With ytterbium(III) triflate; In dichloromethane; for 6h;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.
  • 38
  • [ 1593-60-8 ]
  • [ 408526-05-6 ]
  • [ 1415035-17-4 ]
YieldReaction ConditionsOperation in experiment
63% With iodine; In dichloromethane; water; for 20h;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.
  • 39
  • [ 35476-69-8 ]
  • [ 1593-60-8 ]
  • [ 1415035-04-9 ]
YieldReaction ConditionsOperation in experiment
43% 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.
  • 40
  • [ 35476-69-8 ]
  • [ 1593-60-8 ]
  • [ 1415035-19-6 ]
YieldReaction ConditionsOperation in experiment
31% 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.
  • 41
  • [ 1522-14-1 ]
  • [ 1593-60-8 ]
  • [ 1415035-05-0 ]
YieldReaction ConditionsOperation in experiment
55% 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.
  • 42
  • [ 1522-14-1 ]
  • [ 1593-60-8 ]
  • [ 1415035-20-9 ]
YieldReaction ConditionsOperation in experiment
52% 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.
  • 43
  • [ 1192167-43-3 ]
  • [ 1593-60-8 ]
  • [ 1415035-06-1 ]
YieldReaction ConditionsOperation in experiment
86% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 6h; 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.
  • 44
  • [ 1192167-43-3 ]
  • [ 1593-60-8 ]
  • [ 1415035-21-0 ]
YieldReaction ConditionsOperation in experiment
64% 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.
  • 45
  • [ 1593-60-8 ]
  • [ 94966-45-7 ]
  • [ 1415035-07-2 ]
YieldReaction ConditionsOperation in experiment
85% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 6h; 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.
  • 46
  • [ 1593-60-8 ]
  • [ 94966-45-7 ]
  • [ 1415035-22-1 ]
YieldReaction ConditionsOperation in experiment
67% With iodine; In dichloromethane; water; at 25℃; for 5h; 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.
  • 47
  • [ 1415034-95-5 ]
  • [ 1593-60-8 ]
  • [ 1415035-08-3 ]
YieldReaction ConditionsOperation in experiment
82% With ytterbium(III) triflate; In dichloromethane; at 25℃; for 5h; 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.
  • 48
  • [ 1415034-95-5 ]
  • [ 1593-60-8 ]
  • [ 1415035-23-2 ]
YieldReaction ConditionsOperation in experiment
71% 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.
  • 49
  • [ 18215-68-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-10-7 ]
YieldReaction ConditionsOperation in experiment
46% 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.
  • 50
  • [ 18215-68-4 ]
  • [ 1593-60-8 ]
  • [ 1415035-25-4 ]
YieldReaction ConditionsOperation in experiment
35% 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.
  • 51
  • [ 1415034-96-6 ]
  • [ 1593-60-8 ]
  • [ 1415035-09-4 ]
YieldReaction ConditionsOperation in experiment
30% With ytterbium(III) triflate; In dichloromethane; 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 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.
  • 52
  • [ 1415034-96-6 ]
  • [ 1593-60-8 ]
  • [ 1415035-24-3 ]
YieldReaction ConditionsOperation in experiment
59% 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.
  • 55
  • [ 1593-60-8 ]
  • [ 292638-85-8 ]
  • [ 10154-77-5 ]
YieldReaction ConditionsOperation in experiment
85% With sodium acetate; In methanol; at 60℃; for 18h; General procedure: A mixture of N-phenylsulfonyl hydroxylamine (1a, 173.0 mg, 1.0 mmol), methyl acrylate (2a)(172.0 mg, 2.0 mmol) and NaOAc (82.0 mg, 1.0 mmol) was heated in CH3OH (10.0 mL) at 60 C (oil bath temperature) with stirring for 18 h in a screw-capped thick-walled Pyrex tube under an air atmosphere. After the reaction mixture was cooled to room temperature, it was directly subjected to a short silica column chromatography (2~3 cm, eluted with CH2Cl2) to remove the insoluble materials.To the collected solution, n-octadecane (25.5 mg, 0.1 mmol as internal standard for GC analysis) was then added with stirring. After GC and GC-MS analyses of the mixture, volatiles were then removed under reduced pressure, and the residue was subjected to silica gel column chromatography, eluted with a mixture of solvents of petroleum ether/acetone (from 100:0~100:2 in volume). 3aa was obtained in 212.0 mg (0.93 mmol, 93%) as yellow oil. The GC analysis of reaction mixture revealed the formation of 3aa [19] in 98% GC yield.
75% With sodium acetate; In methanol; at 60℃; for 16h;Sealed tube; <strong>[1593-60-8]N-hydroxy-4-methylbenzenesulfonamide</strong> (187. O mg, 1.0 mmol), methyl acrylate (172. Omg,2. Ommol) with sodium acetate(82. Omg, lmmol) was dissolved in 2 mL of methanol and heated to 60 C in a sealed system (such as a sealed tube)The coupling reaction was carried out for 16 hours. After completion of the reaction, the column chromatography was separated and purified to give a white solid (181. 5 mg, 75%).
 

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