ChemicalBook CAS DataBase List 4-CYANOBENZENESULFONYL CHLORIDE 97

4-CYANOBENZENESULFONYL CHLORIDE 97 synthesis

7synthesis methods

Product Name:4-CYANOBENZENESULFONYL CHLORIDE 97
CAS Number:49584-26-1
Molecular formula:C7H4ClNO2S
Molecular Weight:201.63

150993-53-6

49584-26-1

N-Chlorosuccinimide (NCS, 1.778 g, 13.32 mmol) was slowly added to a suspension of 4-(benzylthio)benzonitrile (1 g, 4.44 mmol) dissolved in acetic acid (AcOH, 10 mL) and water (3.5 mL) at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc), washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a hexane solution of 15%-20% ethyl acetate as eluent to give a white solid. The resulting solid was washed with hexane and dried under reduced pressure to give 4-cyanobenzenesulfonyl chloride (0.701 g, 3.48 mmol, 78% yield) as a white solid. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.91-7.97 (2H, m), 8.15-8.21 (2H, m).

36801-01-1 Synthesis

36801-01-1
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Yield:49584-26-1 99%

Reaction Conditions:

with N-chloro-succinimide;isopropyl alcohol in dichloromethane at 0 - 20; for 1 h;

Steps:

General procedure for the preparation of sulfonyl halides from thiols
General procedure: To a stirred solution of the corresponding thiol 1 (1 eq) [1]^a and isopropanol (CAS: 67-63-0) (2 eq) in dichloromethane [2] (0.15 M), N-bromosuccinimide (CAS: 128-08-5) or N-chlorosuccinimide (CAS: 128-09-6) (4 or 3.5 equiv) was added portion wise^1b at rt (in the case of NBS) or 0 °C (in the case of NCS). The reaction mixture is stirred at rt until starting material was not visible by TLC (approx. 1 h). Then, the mixture was diluted with cold, saturated NaHCO₃, and extracted with EtOAc (x4).^1c The combined organic extracts were dried over anh. Na₂SO₄ and concentrated in vacuo to afford the crude material. Filtration on a SiO₂ column or radial chromatography using mixtures of hexanes/ethyl acetate/acetone as eluents, yielded the pure sulfonyl halides 2 or 3.

References:

Silva-Cuevas, Carolina;Perez-Arrieta, Carlos;Polindara-García, Luis A.;Lujan-Montelongo, J. Armando [Tetrahedron Letters,2017,vol. 58,# 23,p. 2244 - 2247] Location in patent:supporting information

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150993-53-6 Synthesis

150993-53-6
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49584-26-1
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References