4-Fluoro-N,N-dimethylbenzenesulfonamide

4-Fluoro-N,N-dimethylbenzenesulfonamide Property

Boiling point:

279.6±42.0 °C(Predicted)

Density 

1.276±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-4.87±0.70(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H10FNO2S/c1-10(2)13(11,12)8-5-3-7(9)4-6-8/h3-6H,1-2H3

InChIKey

WURMPFYVFDHATI-UHFFFAOYSA-N

SMILES

C1(S(N(C)C)(=O)=O)=CC=C(F)C=C1

Safety

HS Code 

2935909099

Hazard and Precautionary Statements (GHS)

4-Fluoro-N,N-dimethylbenzenesulfonamide Chemical Properties,Usage,Production

Synthesis

GENERAL STEPS: A mixture of 4-fluorobenzenesulfonyl chloride (2.0 g, 10.3 mmol), dimethylamine (2.0 M in methanol, 11.0 mL, 22.0 mmol), and dichloromethane (11.0 mL) was stirred at 0 °C, followed by continued stirring at room temperature for 5 min. Dichloromethane (30 mL) was added to dilute the reaction mixture. The organic phase was washed sequentially with 1 M hydrochloric acid (30 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate and filtered. The solvent was removed by concentration under reduced pressure to give 4-fluoro-N,N-dimethylbenzenesulfonamide as a white solid (2.12 g, quantitative yield). A mixture of 4-fluoro-N,N-dimethylbenzenesulfonamide (1.50 g, 7.39 mmol), sodium thiosulfate (2.08 g, 29.7 mmol), and N,N-dimethylformamide (9.0 mL) was placed in a sealed tube and the reaction was stirred for 16 h at 170 °C. The reaction was completed by cooling to room temperature. After completion of the reaction, it was cooled to room temperature and 1 M sodium hydroxide solution (40 mL) was added. The aqueous phase was washed with ether (2 x 40 mL) and subsequently acidified with 2M hydrochloric acid to pH < 2 and extracted with ether (3 x 40 mL). The organic phases were combined, dried over anhydrous magnesium sulfate and filtered. The solvent was removed by concentration under reduced pressure to afford 4-mercapto-N,N-dimethylbenzenesulfonamide as an orange oil (503 mg, 31% yield).1H NMR (500 MHz, CDCl3) δ 7.67-7.58 (m, 2H), 7.43-7.35 (m, 2H), 3.67 (s, 1H), 2.71 (s, 6H).

References

[1] Patent: EP1354882, 2003, A1. Location in patent: Page/Page column 85
[2] Patent: WO2017/141049, 2017, A1. Location in patent: Paragraph 00728
[3] Patent: WO2010/92043, 2010, A1. Location in patent: Page/Page column 120
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7299 - 7317
[5] Patent: EP1757582, 2007, A1. Location in patent: Page/Page column 31