84461-21-2

Usage

InChI:InChI=1/C7H8O3S.C3H9N/c1-6-2-4-7(5-3-6)11(8,9)10;1-3(2)4/h2-5H,1H3,(H,8,9,10);3H,4H2,1-2H3

Upstream product

• 563-83-7 ISOPROPYLAMIDE 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 22685-19-4 diethyl N-isopropylphosphoramidate 
• 104-15-4 toluene-4-sulfonic acid 
• 102095-58-9 C₁₂H₂₆NO₅P 
• 75-31-0 isopropylamine 

Downstream Products

• 21230-07-9 N-isopropyl-p-toluenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

One-Pot synthesis of sulfonamides from primary and secondary amine derived sulfonate salts using cyanuric chloride

A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields. Georg Thieme Verlag Stuttgart.

New protocol for converting alcohols into amines

The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1, diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.

THE REACTION OF ETHYL-FORMIMIDATE WITH GRIGNARD REAGENTS: A NEW APPROACH TO ELECTROPHILIC AMINATION

Addition of Grignard reagents to ethyl-N-(diethoxyphosphoryl)formimidate, 3 followed by aqueous workup and treatment of the resultant diethyl phosphoramidates with p-toluenesulfonic acid in ethanol gives, depending upon the organomagnesium reagent used, the corresponding tosylates of primary or secondary amines in moderate to good yields.The diethoxyphosphoryl moiety remains unchanged upon treatment of 3 with Grignard reagents.Key words: Diethyl-(N-alkylphosphoramidates); Grignard reagents; ammonium tosylates; substitution-addition; substitution-reduction; electrophilic amination.

Direct Conversion of Aliphatic Carboxamides to Alkylammonium Tosylates with benzene

The utility of benzene (2) as a "Hofmann reagent" has been explored.Treatment of various primary, aliphatic carboxamides (RCONH2, R = methyl, ethyl, isopropyl, tert-butyl, n-pentyl, n-heptyl, undecyl, allyl, benzyl, cyclobutyl, cyclohexyl) with 2 in acetonitrile at reflux gave the corresponding alkylammonium tosylates (RN+H3-OTs) in yields ranging from 57percent to 94percent.The alkylammonium tosylates separated directly from the solvent when the reaction mixtures were kept at room temperature or below.When α-phenylacetamide was allowed to react with 2 in ethanol, ethyl benzylcarbamate (4) was obtained in 50percent yield, a result consistent with the intermediate existence of benzyl isocyanate in this reaction.A mechanism for the conversion of carboxamides by 2 to alkylammonium tosylates, involving the initial formation of N-phenyl iodonio amides and their collapse to iodobenzene and alkyl isocyanates, is proposed.The reaction of malonamide with 2 in acetonitrile followed a divergent course: 2-(tosyloxy)malonamide (3) was obtained in ca. 81percent yield (crude).