17262-66-7

Basic information

• Product Name: N-{4-[bis(2-chloroethyl)sulfamoyl]phenyl}acetamide
• CAS NO: 17262-66-7
• Molecular Formula: C₁₂H₁₆Cl₂N₂O₃S
• Molecular Weight: 339.238
• Mol File: 17262-66-7.mol
• Article Data: 3

Chemical Properties

• Density: 1.391g/cm³
• Refractive Index: 1.575
• CAS DataBase Reference: N-{4-[bis(2-chloroethyl)sulfamoyl]phenyl}acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{4-[bis(2-chloroethyl)sulfamoyl]phenyl}acetamide(17262-66-7)
• EPA Substance Registry System: N-{4-[bis(2-chloroethyl)sulfamoyl]phenyl}acetamide(17262-66-7)

Safety Data

• Hazardous Substances Data: 17262-66-7(Hazardous Substances Data)

Upstream product

• 17262-65-6 N-(4-(N,N-bis(2-hydroxyethyl)sulfamoyl)phenyl)acetamide 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 

Downstream Products

• 24336-65-0 Sulfanilsaeure-(2,2'-dichlor-diethylamid) 
• 1357621-17-0 N,N-bis[2-(4-cyano-2-methoxyphenoxy)ethyl]-4-acetamidobenzenesulfonamide 
• 1147077-69-7 N,N-bis[2-(4-cyanophenoxy)ethyl]-4-(acetylamino)benzenesulfonamide 
• 25715-22-4 sulfanilic acid-[bis-(2-chloro-ethyl)-amide]; hydrochloride 

Relevant articles and documents

Structural analysis of bis-amidines and bis-nitriles in solid-state by combining NMR spectroscopy and molecular modeling

The paper presents the analysis of the structures of four novel sulfonamide-based bis-amidines, and four novel interesting intermediates leading to them, named bis-nitriles, in solid-state based on 13C CP/MAS NMR spectroscopy and theoretical calculations of shielding constants at DFT level of theory. We have observed double 13C resonances in solid-state spectra as compared with solution spectra. The considerations of experimental chemical shifts followed by shielding computations allowed us to define essential geometric details regarding the most probable conformations in solid-state. All compounds have one independent molecule in the asymmetric unit, and a main reason of splittings of NMR signals in solid-state is different orientation of alkoxy fragments (methyl groups and linker) with reference to benzene rings.

A novel kind of antitumour drugs using sulfonamide as parent compound

To obtain potent antitumour agents with low toxicity, sulfonamide derivatives containing 5-flurouracil and nitrogen mustard, respectively are designed and synthesised. 1-(3-(4-Acetylaminobenzenesulfonamido)-3-oxopropyl)-5-fluoropyrimidine-2, 4-dione (4) was obtained by the coupling of p-acetamidobenzenesulfonamide with 3-(5-fluorouracil-1-yl) propionic acid. The hydrolysis of 4 led to 1-(3-(4-aminobenzenesulfonamido)-3-oxopropyl)-5-fluoropyrimidine-2,4-dione (5). Treatment of p-acetamidobenzenesulfonyl chloride with bis(2-chloroethyl) amine led to 4-acetylamino-N,N-bis(2-chloroethyl)benzenesulfonamide (6). Subsequent hydrolysis of 6 in hydrochloric acid led to 4-amino-N,N-bis(2-chloroethyl)benzenesulfonamide hydrochloride (7). Two different synthetic route were investigated in the synthesis of 2-[N1-2-pyrimidyl-aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate (12b). Carbobenzyloxy was proved to be unsuitable for the protection of the aromatic amino group of sulfadiazine since the pyrimidine ring was also hydrogenated at the last step of the first route under the deprotection condition. In another route, acetyl was firstly used as the protective group, then it was replaced by the Schiff's base. The reaction of chlorambucil with 2-[N1-2-pyrimidinyl-(p-acetyl)aminobenzenesulfonamido] ethanol (10b) afforded 2-[N1-2-pyrimidinyl-(p-benzylidene)aminobenzenesulfonamido] ethyl 4-bis(2-chloroethyl) aminophenyl butyrate (11b). Compound 12b was obtained by the hydrolysis of 11b. The acute toxicity and antitumour activity of 5, 7 and 12b have been investigated in mice. Compound 12b exhibited high antitumour activity and low toxicity with a therapeutic index (TI) of 47.55.