Alternatived Products of [ 5033-21-6 ]
Product Details of [ 5033-21-6 ]
| CAS No. : | 5033-21-6 |
MDL No. : | MFCD00447613 |
| Formula : |
C10H13NO3S
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
227.28
|
Pubchem ID : | - |
| Synonyms : |
|
Application In Synthesis of [ 5033-21-6 ]
* 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 [ 5033-21-6 ]
- 1
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[ 110-91-8 ]
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[ 873-55-2 ]
-
[ 5033-21-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 98% |
With iodine In 1,2-dichloro-ethane at 25℃; for 20h; |
|
| 95% |
Stage #1: sodium benzenesulfonate With iodine at 20℃; for 0.333333h; Green chemistry;
Stage #2: morpholine In ethanol at 20℃; for 3h; Green chemistry; |
|
| 82% |
With phenyltrimethylammonium tribromide In tetrahydrofuran at 30℃; for 7h; |
General experimental procedure (A) for the synthesis of sulfonamides
General procedure: To a well stirred solution of sodium sulfinate(1equiv.) in THF Phenyl Trimethyl ammonium Tribromide (PTAB)(1equiv.) was added and stirred about 5 minutes, The amine (1 equiv.) was then added to the reaction mixture and the reaction mixture was stirred for 6-8 hrs at room temperature. After completion of the reaction which was monitored with TLC, the reaction mixture was quenched with distilled water and extracted with ethyl acetate (3X3ml). The organic fraction was washed with saturated brine solution and dried over oven dried anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. The residual crude mass was then subjected to column chromatography over silica gel, Elution with proper solvent mixture afforded the desired sulfonamide as the pure product. |
| 78% |
With tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; methanol at 20℃; for 12h; |
A Typical Procedure for the Preparation of Sulfonamides
General procedure: (0.45 mmol), amines 2 (0.30 mmol), (n-Bu)4NBr (0.36 mmol),and m-CPBA (0.3 mmol) were added successively. The suspensionmixture was vigorously stirred at r.t. for 12 h. Upon completion,the reaction was quenched by addition of sat. aqNa2S2O3 (2 mL), sat. aq Na2CO3 (8 mL), and H2O (5 mL), respectively.The mixture was extracted with CH2Cl2 (3 × 5 mL) andthe combined organic phase was dried over anhydrous Na2SO4,filtered, and concentrated under reduced pressure. The residuewas then purified on a silica gel plate (PE-EtOAc = 3:1) tofurnish products 3. |
| 78% |
With 1-iodo-propane; 3-chloro-benzenecarboperoxoic acid In 2,2,2-trifluoroethanol at 20℃; for 4h; |
General procedure for the synthesis of sulfonamides
General procedure: Sodium sulfinates 1 (1.0 mmol), amines 2 (1.5 mmol), 1-iodopropane (0.2 mmol), and mCPBA (1.5 mmol) were added successively into CF3CH2OH (5.0 mL). The suspension mixture was vigorously stirred at room temperature for 4 h. Upon completion, the reaction mixture was quenched by addition of sat. aq. Na2S2O3 (3 mL), sat. aq. Na2CO3 (8 mL) and H2O (10 mL), respectively. The mixture was extracted with CH2Cl2 (320 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered,and concentrated under reduced pressure. The residue was then purified on a silica gel plate (3:1 petroleum ether-ethyl acetate) to furnish the products 3. |
| 75% |
With sodium hypochlorite In water Ambient temperature; |
|
| 27% |
With copper(ll) bromide In acetonitrile at 50℃; for 12h; |
|
| 27% |
With copper(ll) bromide In acetonitrile at 50℃; for 12h; |
|
Reference：
[1]Wei, Wei; Liu, Chunli; Yang, Daoshan; Wen, Jiangwei; You, Jinmao; Wang, Hua
[Advanced Synthesis and Catalysis, 2015, vol. 357, # 5, p. 987 - 992]
[2]Yang, Kai; Ke, Miaolin; Lin, Yuanguang; Song, Qiuling
[Green Chemistry, 2015, vol. 17, # 3, p. 1395 - 1399]
[3]Sarkar, Debayan; Ghosh, Manoj Kumar; Rout, Nilendri
[Tetrahedron Letters, 2018, vol. 59, # 24, p. 2360 - 2364]
[4]Wu, Sixue; Zhang, Yikun; Zhu, Min; Yan, Jie
[Synlett, 2016, vol. 27, # 19, p. 2699 - 2704]
[5]Zhou, Zhongshi; He, Xuehan
[Phosphorus, Sulfur and Silicon and the Related Elements, 2020, vol. 195, # 4, p. 280 - 284]
[6]Scully, Frank E.; Bowdring, Katherine
[Journal of Organic Chemistry, 1981, vol. 46, p. 5077 - 5081]
[7]Chung, Sohyun; Kim, Jinho
[Tetrahedron Letters, 2019, vol. 60, # 11, p. 792 - 795]
[8]Current Patent Assignee: INCHEON NATIONAL UNIVERSITY - KR2021/33367, 2021, A
Location in patent: Paragraph 0073; 0076
- 2
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[ 688798-57-4 ]
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[ 5033-21-6 ]
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[ 1610528-66-9 ]
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[ 1610528-67-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 11% |
With palladium diacetate; potassium carbonate In N,N-dimethyl acetamide at 150℃; for 16h; Schlenk technique; Inert atmosphere; |
|
- 3
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[ 688798-57-4 ]
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[ 5033-21-6 ]
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[ 1610528-66-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
With palladium diacetate; potassium pivalate In N,N-dimethyl acetamide at 150℃; for 16h; Schlenk technique; Inert atmosphere; |
|
- 4
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[ 688798-57-4 ]
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[ 5033-21-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium <i>tert</i>-butylate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Schlenk technique; Inert atmosphere; |
|
- 5
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[ 1696-20-4 ]
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[ 873-55-2 ]
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[ 5033-21-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
Stage #1: 4-acetylmorpholine With potassium <i>tert</i>-butylate In acetonitrile at 50℃; for 0.5h; Schlenk technique; Green chemistry;
Stage #2: sodium benzenesulfonate With N-iodo-succinimide In acetonitrile at 50℃; for 12h; Schlenk technique; Green chemistry; |
2. General procedure for synthesis of sulfonamides from sodium sulfinates and formamides
General procedure: An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with formamide 1 (2.0 mmol), KO-t-Bu (2.0 mmol) and CH3CN (2.0 mL). The mixture was stirred at 50 °C for 30 min and then a CH3CN (2.0 mL) solution containing sodium sulfinates 2 (0.5 mmol) and NIS (1.0 mmol) was slowly added dropwise. The resulting solution stirred at 50 °C for 12 h under air. The mixture was then cooled to room temperature, diluted with 30 mL of H2O, and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the products. |
Reference：
[1]Bao, Xiaodong; Rong, Xiaona; Liu, Zhiguo; Gu, Yugui; Liang, Guang; Xia, Qinqin
[Tetrahedron Letters, 2018, vol. 59, # 29, p. 2853 - 2858]
- 6
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[ 110-91-8 ]
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[ 5535-48-8 ]
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[ 5033-21-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
Stage #1: morpholine With N-Bromosuccinimide; tetraethylammoniumcyanide In dichloromethane
Stage #2: PVS In dichloromethane at 20℃; for 1h; |
General Procedure for the Synthesis of Sulfonamides 4a-f
General procedure: N-Bromosuccinimide (1.5 equiv, 0.6 mmol) was added portionwiseto a vial containing a solution of an appropriate amine (1.5equiv, 0.6 mmol) in DCM (1 mL). In another vial, vinyl sulfone(0.4 mmol) and tetraethylammonium cyanide (1.05 equiv, 0.42mmol) were taken together with DCM (1 mL) and stirred for 5min. The later solution was then added dropwise to the formermixture. The combined reaction mixture was allowed to stir atroom temperature. After completion of the reaction (checked bycrude 1H NMR and TLC), water (10 mL) was added to the reactionmixture, and the product was extracted with ethyl acetate(3 × 10 mL). The combined organic layers were washed withbrine (10 mL), dried over anhydrous Na2SO4, and concentratedunder vacuum. The crude product thus obtained was purifiedby column chromatography using 10-20% ethyl acetate inpetroleum ether. |
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