343581-97-5

Basic information

• Product Name: N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide
• Synonyms: N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide
• CAS NO: 343581-97-5
• Molecular Weight: 287.38
• Mol File: 343581-97-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide(343581-97-5)
• EPA Substance Registry System: N,N-bis(2-methoxyethyl)-4-methylbenzenesulfonamide(343581-97-5)

Safety Data

• Hazardous Substances Data: 343581-97-5(Hazardous Substances Data)

Upstream product

• 111-95-5 Bis-(2-methoxyethyl)amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 197803-54-6 2-methyl-5-nitropyrimidine-4,6-bis(p-toluenesulfonate) 

Downstream Products

• 111-95-5 Bis-(2-methoxyethyl)amine 
• 6339-26-0 4-tosylmorpholine 
• 115-10-6 Dimethyl ether 

Relevant articles and documents

Hydrogen-Bonding Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers over Ionic Liquid under Metal-Free Conditions

O-heterocycles have wide applications, and their efficient and green synthesis is very interesting. Herein, we report hydrogen-bonding catalyzed ring-closing metathesis of aliphatic ethers to O-heterocycles over ionic liquid (IL) catalyst under metal- and solvent-free conditions. The IL 1-butylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3H-BMIm][OTf]) is discovered to show outstanding performance, better than the reported catalysts. An interface effect plays an important role in mediating the reaction rate due to the immiscibility between the products and the IL catalyst, and the products can be spontaneously separated. NMR analysis and DFT calculation suggest that a pair of cation and anion of [SO3H-BMIm][OTf] could form three strong H-bonds with an ether molecule, which catalyze the ether transformation via a cyclic oxonium intermediate. A series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines and dioxane can be obtained from their corresponding ethers in excellent yields (e.g., >99 %). This work opens an efficient and metal-free way to produce O-heterocycles from aliphatic ethers.

METHOD FOR DEPROTECTING ARYL OR ALKYL SULFONAMIDES OF PRIMARY OR SECONDARY AMINES

The invention relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by contacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material in the presence of a solid proton source under conditions sufficient to form the corresponding amine. The invention also relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by a) reacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material, and b) subsequently reacting the reaction product from step a) with an electrophile or a proton source. Preferred Stage 0 or Stage I alkali metal-silica gel materials include Na, K2Na, and Na2K.

Unsymmetrical 4,6-diamino-2-methyl-5-nitropyrimidine synthesis via 4,6-bis(tosylates)

Chlorides have traditionally been used as leaving groups for the introduction of 4- and 6-heteroatomic substituents onto pyrimidines. Use of 4,6-dichloro-2-methyl-5-nitropyrimidine allows the sequential introduction of different 4- and 6-heteroatomic substituents onto this core; however, this reagent is highly hazardous to handle. We have found that the analogous 4,6-bis(tosylate) offers a less hazardous substance which undergoes the same nucleophilic aromatic substitution chemistry as the dichloride, including sequential introduction of different nucleophiles.