2-CHLORO-5-NITROBENZENESULFONAMIDE Chemical Properties

Melting point:

180-183°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

color 

White

InChIKey

ZAJALNCZCSSGJC-UHFFFAOYSA-N

CAS DataBase Reference

96-72-0(CAS DataBase Reference)

2-CHLORO-5-NITROBENZENESULFONAMIDE Usage And Synthesis

Chemical Properties

White Solid

Uses

2-Chloro-5-nitrobenzenesulfonamide (cas# 96-72-0) is a compound useful in organic synthesis.

Synthesis

Example 17A-1 Synthesis of 2-chloro-5-nitrobenzenesulfonamide: 2-chloro-5-nitrobenzenesulfonic acid (104 g, 437.6 mmol) was dissolved in thionyl chloride (240 mL), followed by the addition of N,N-dimethylformamide (2 mL) as a catalyst. The reaction mixture was heated to reflux and maintained for 4 hours to complete the reaction. Upon completion of the reaction, the mixture was carefully poured into water for quenching and the product was subsequently isolated by filtration. The resulting 2-chloro-5-nitrobenzenesulfonyl chloride was dissolved in toluene and slowly added to a pre-mixed solution of NH4OH (520 mL) and tetrahydrofuran (520 mL) at -10 °C. The reaction mixture was stirred at this temperature for 1 h. The reaction was quenched with 6 M hydrochloric acid solution and the final pH was adjusted to 4. After separating the aqueous and organic layers, the organic layer was concentrated to dryness to give a powdery product. To this powdered product pentane was added and the target compound was isolated by filtration and dried to give 2-chloro-5-nitrobenzenesulfonamide (82.6 g, 80% yield).

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 18 - 26
[2] Patent: US2011/152246, 2011, A1. Location in patent: Page/Page column 293
[3] Patent: US2005/107364, 2005, A1. Location in patent: Page/Page column 75
[4] Patent: WO2005/19191, 2005, A2. Location in patent: Page/Page column 151
[5] Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 5, p. 669 - 680

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