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Chemical Structure| 19837-92-4 Chemical Structure| 19837-92-4

Structure of 19837-92-4

Chemical Structure| 19837-92-4

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Product Details of [ 19837-92-4 ]

CAS No. :19837-92-4
Formula : C14H13ClN2O3S
M.W : 324.78
SMILES Code : CC(NC1=CC=C(S(=O)(NC2=CC=C(Cl)C=C2)=O)C=C1)=O

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Application In Synthesis of [ 19837-92-4 ]

* 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 [ 19837-92-4 ]

[ 19837-92-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 19837-92-4 ]
  • [ 16803-92-2 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride; In water; at 100℃; for 6h; General procedure: A mixture of 0.006 mol of the respective N-(4-(N-arylsulfamoyl)phenyl)acetamide 43a-g in 30 mL of 6 N HCl was kept with stirringunder reflux (100 C) for 6 h. Then, the solution was cooled andneutralized with 20% NaOH. The precipitate formed was vacuumfiltered, washed with water and recrystallized from ethanol/water(1:1).
64% With hydrogenchloride; In acetone; at 20℃; for 0.0833333h;Cooling with ice; General procedure: To a solution of the acetamide 2a-f (1 eq) in EtOH (2 mL/mmol) was added concentratedHCl (1 mL/mmol), the mixture was stirred at 75 C overnight, diluted with water andbasified with 0.2 N NaHCO3 at 0 C to pH = 8. The reaction mixture was filtered andwashed with cold water. The residue was then recrystallized in EtOH and filtered to givethe title compound.
With hydrogenchloride; In ethanol; water; at 75 - 80℃; for 4h; General procedure: Synthesis of the precursor sulfonamides 4a- 4c was achieved bytreating 0.01 mol of substituted aromatic amines (3a-3c) with0.015 mol of 4-(acetylamino)benzene sulfonylchloride (2) in0.03 mol of pyridine at room temperature (RT) for 8 h. Reaction progress was monitored by TLC (with hexane: EtOAc (1:1) mixtureas eluent. Excess pyridine was neutralized with diluted HCl solutionand the product was isolated by filtration. The hydrolysis of theabove product was carried out by refluxing it with concentrated HCl in ethanol for 4 h. The clear solution was cooled and neutralized by ammonium hydroxide solution. The solid precipitated was filtered and dried at 50-55 C (Scheme 1).
With hydrogenchloride; at 100℃; for 2h; General procedure: 3-/4-Acetamidobenzenesulfonyl chloride (1, 1 equiv.) was dissolved in dichloromethane (80mL) at 0C. An appropriate aniline (1.05 equiv.) and triethylamine (2 equiv.) were added to the solution dropwise. Then, the mixture was stirred for 2h at room temperature. TLC monitored reaction progress. After reaction completed, 2N HCl and Brine solution were added to the mixture. The residue was obtained by washing the mixture with water and dichloromethane and the solid recovered by filtration. The compound was added to 12N HCl, heated to reflux and stirred for 2h. Cooled to room temperature, the mixture was washed by NaOH, and extracted with dichloromethane (3×30mL) and methanol (3×30mL). Combined organic layers were dried over magnesium sulfate and concentrated under vacuum. The crude products were purified by a silica-gel column chromatography. 4a [15], 4b [20], 4c [21], 4d [21], 4e [17], 4f [22], 4g [17], 4h [15], 4i [23], 4j [21], 4k [24], 4l [25], 4m [26].

 

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