21094-70-2

Usage

Uses

Used in Pharmaceutical Industry:
2-BENZENESULFONYLMETHYL-1H-BENZOIMIDAZOLE is used as an active pharmaceutical ingredient for the development of medications for treating fungal and bacterial infections due to its antifungal and antimicrobial properties.
Used in Anti-inflammatory Applications:
2-BENZENESULFONYLMETHYL-1H-BENZOIMIDAZOLE is used as a potential anti-inflammatory agent, as research has shown that it may possess anti-inflammatory properties.

InChI:InChI=1/C14H12N2O2S/c17-19(18,11-6-2-1-3-7-11)10-14-15-12-8-4-5-9-13(12)16-14/h1-9H,10H2,(H,15,16)

Upstream product

• 615-15-6 2-Methyl-1H-benzimidazole 
• 98-09-9 benzenesulfonyl chloride 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 1009099-84-6 4-(phenylsulfonyl)-1-(trifluoromethyl)pyrido[1,2-a]benzimidazole 
• 60987-26-0 6-(phenylsulfonyl)-benzimidazo[1,2-a]quinoline 

Relevant academic research and scientific papers

Zinc-mediated tandem-one-pot facile synthesis of 1-(arylsulfonyl) aryl/heteryl methanes: A case of C-S bond formation

Reaction of arylmethyl/heteryl methyl zinc chloride (generated in situ from aryl methyl and heteryl methyl chloride and zinc metal) with aryl sulfonyl chlorides in tetrahydrofuran (THF) under mild conditions (i.e., at room temperature) furnishes the corresponding 1-(aryl sulfonyl)aryl/heteryl methanes in good yields.

A facile solvent-free synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonyl alkyl) benzimidazoles using "tBAB" as surface catalyst

Reaction 2-(α-chloroalkyl)benzimidazoles 1 with aryl sulphinate sodium salt 2 under solvent-free conditions in the presence of tetrabutylammonium bromide as surface catalyst, by simple physical grinding using mortar and pestle, gives 1H-2-(α-arylsulfonylalkyl)benzimidazoles 3. The latter on treatment with alkylating agents under solvent-free conditions results in 1-alkyl/aralkyl-2-(α-arylsulfonylalkyl)benzimidazoles 4. Alternatively, 4 can also be prepared directly from 1-alkyl/aralkyl-2-(α- chloroalkyl)benzimidazoles 5 by reaction with 2, which in turn could be prepared by reaction of 1 with alkylating agents under solvent-free conditions and all these reactions are free from organic solvents including experimental procedures.

Synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonylalkyl)benzimidazoles under PTC conditions

2-(α-chloroalkyl)benzimidazoles 1 on reaction with arylsulphinate sodium salt 2, in CH3CN under PTC conditions, gives 3 which on alkylation yields 1-alky/aralkyl-2-(α-aryl sulfonylalkyl)benzimidazoles 4. Alternatively, 4 can also be prepared by the reaction of 2 with 1-alkyl/aralkyl-2-(α-chloroalkyl)benzimidazole 5 in CH3CN using triethylbenzylammonium chloride (TEBAC) as PTC. 5 are obtained from 1 in turn, by alkylation in CH3CN under PTC conditions.

Polyethyleneglycol Catalysed N-Sulphonylation and N-Benzoylation of Substituted Benzimidazoles

Benzenesulphonyl chloride and p-toluenesulphonyl chloride react with benzimidazole and 2-phenylbenzimidazole in benzene and 50percent aqueous sodium hydroxide in the presence of polyethyleneglycol 400 or triethylbenzylammonium chloride to afford the corresponding N-sulphonyl derivatives.However, 2-methylbenzimidazole affords both N-sulphonylated and C-sulphonylated products.N-Benzoylation is also effected under similar conditions using benzoyl chloride.