102520-41-2

Upstream product

• 28446-58-4 but-3-enamide 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 104-15-4 toluene-4-sulfonic acid 
• 107-11-9 1-amino-2-propene 
• 146039-11-4 Allyl-phosphorimidic acid triethyl ester 
• 85231-93-2 C₁₂H₂₄NO₅P 

Downstream Products

• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1532554-95-2 methyl 4-ammoniumbut-2-enoate tosylate 

Relevant academic research and scientific papers

An optimized version of Gabriel-type nucleophilic amination

N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t- butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-I. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol-affords ammonium tosylates 3a-I in reasonable yields.

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.

TRIETHYL PHOSPHITE IN ORGANIC SYNTHESIS. A FACILE, ONE-POT CONVERSION OF ALCOHOLS INTO AMINES

General protocols for converting primary, secondary, and tertiary alcohols into the corresponding primary amines are presented.

Optimized procedures for one-pot conversion of alkyl bromides into amines via the Staudinger reaction

New optimized procedures for transforming primary and secondary alkyl bromides into the corresponding primary amine salts have been elaborated. Essential modifications of azidation and deprotection of intermediate triethoxyphosphine alkylimides resulted in substantial improvement of the overall yields. Conversion of ammonium tosylates and hydrochlorides into free amines in a nonaqueous medium is described.

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).