N-(4-Fluorophenyl)-2-nitrobenzenesulfonamide synthesis
- Product Name:N-(4-Fluorophenyl)-2-nitrobenzenesulfonamide
- CAS Number:159048-81-4
- Molecular formula:C12H9FN2O4S
- Molecular Weight:296.27
Yield:159048-81-4 76%
Reaction Conditions:
with pyridine in dichloromethane at 0 - 20; for 0.5 h;
Steps:
4.1.2. General procedure for intermediates 12-19
General procedure: To a solution of aniline (23 mL, 249 mmol, 1.1 eq) and pyridine(22 mL, 271 mmol, 1.2 eq) in anhydrous DCM (200 mL) was added a solution of 2-nitrobenzenesulfonyl chloride (50.0 g,226 mmol, 1.0 eq) in anhydrous DCM (200 mL) dropwise at 0° C.The resultant mixture was stirred at room temperature for 0.5 hand then quenched with dilute hydrochloric acid (1 N). After filtration, the filtrate was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was ultimately subjected to recrystallization with EtOH to provide N-phenyl-2-nitrobenzenesulfonamide 12 as a light yellow solid. Yield 83%; ESI-MS: m/z 279 [MH]. Intermediates 13-19 were prepared ina procedure similar to that described for 12.
References:
Ma, Xiaodong;Wei, Jun;Wang, Chang;Gu, Dongyan;Hu, Yongzhou;Sheng, Rong [European Journal of Medicinal Chemistry,2019,vol. 170,p. 112 - 125]
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