4115-16-6

Upstream product

• 2227-79-4 benzenecarbothioamide 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 51673-52-0 C₁₄H₁₃ClN₂O₂S 
• 2403-55-6 4-(2-methyl-1-propenyl)morpholine 
• 51673-52-0 N-chloro-N'-tosylbenzamidine 
• 941-55-9 4-toluenesulfonyl azide 
• 536-74-3 phenylacetylene 
• 24401-44-3 β-Piperidino-α-methyl styrene 
• 1670-14-0 benzamidine monohydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 28478-27-5 4-(2-phenyl-propenyl)-morpholine 
• 4513-27-3 N-(tolylsulfonyl)benzimidoyl chloride 
• 100-47-0 benzonitrile 
• 874-90-8 4-methoxybenzonitrile 

Downstream Products

• 51673-52-0 C₁₄H₁₃ClN₂O₂S 
• 90095-45-7 C₁₄H₁₂Cl₂N₂O₂S 
• 110967-03-8 N¹-2,4-dinitrophenyl-N²-(p-tolylsulfonyl)benzamidine 
• 90095-48-0 C₁₄H₁₂Cl₂N₂O₂S₂ 
• 90119-97-4 C₂₂H₂₈N₄O₄S₂ 
• 51673-52-0 N-chloro-N'-tosylbenzamidine 
• 82719-89-9 N-Benzoyl-N-{phenyl-[(Z)-toluene-4-sulfonylimino]-methyl}-benzamide 
• 71734-84-4 N-{Phenyl-[(Z)-toluene-4-sulfonylimino]-methyl}-benzamide 

Relevant academic research and scientific papers

Direct Transformation of Terminal Alkynes into Amidines by a Silver-Catalyzed Four-Component Reaction

An unprecedented conversion of terminal alkynes into N-sulfonimidamides (amidines) is reported by a silver-catalyzed, one-pot, four-component reaction with TMSN3, sodium sulfinate, and sulfonyl azide. The reaction scope includes both aromatic and aliphatic alkynes. A possible cascade reaction mechanism, consisting of alkyne hydroazidation, sulfonyl radical addition, 1,3-dipolar cycloaddition by TMSN3, and retro-1,3-dipolar cycloaddition, is proposed. TMSN3 is found to play an essential role in each step of the reaction.

Guanidine Synthesis: Use of Amidines as Guanylating Agents

The use of amidines for the tandem or one-pot synthesis of guanidines is reported. Guanidines are obtained by oxidative rearrangement of readily available and stable amidines into carbodiimides, followed by in situ reaction with amines. The protocol can be executed under mild reaction conditions (30°C), in a green solvent (dimethyl carbonate). The amine scope is broad, including sterically hindered, oxidation-sensitive and chiral amines. Examples for the synthesis of both acyclic and cyclic guanidines are provided. 2-Propoxyphenyl iodide (2-PrOPhI) by-product, generated from the oxidant [N-(p-toluenesulfonyl)imino](2-propoxyphenyl)iodinane (2-PrOPhINTs), can be isolated in high yields making regeneration of the hypervalent iodine reagent possible. The utility and greenness of the synthetic method versus the state-of-the-art is demonstrated by a new route towards the antihypertensive drug Pinacidil. The process mass intensity (PMI) of the new route is only 24% of the classical one.

N-HALOAMIDINES.VI. REACTION OF N-CHLORO-N'-BENZENESULFONYLBENZAMIDINES WITH ENAMINES.

The reaction between N-chloro-N'-benzenesulfonylbenzamidines and β,β-disubstituted enamines affords N-(benzenesulfonyl)-N'--benzamidines.When both β-substituents are methyl groups the open chain adducts have been isolated and characterized, whereas, when one of the two substituents is a phenyl group, they have been characterized only by PMR because of the easy cyclization to 1-benzenesulfonyl-4,5-dihydroimidazoles.

REACTION OF N-CHLORO-N'-ARYLSULFONYL- AND N'-BENZOYLBENZAMIDINES WITH SULFUR AND SULFUR DICHLORIDE

N-(N'-Arylsulfonylbenzimidoyl)dichlorosulfimides are obtained in the reaction of N-chloro-N'-arylsulfonylbenzamidines with sulfur or sulfur dichloride.N-Chloro-N'-benzoylbenzamidine reacts with sulfur dichloride in the presence of pyridine to form N-(N'-benzoylbenzimidoyl)dichlorosulfimide.Thermolysis of the latter gives 1,3,5-triphenyl-sym-triazine.When N-chloro- or N,N-dichloro-N'-benzoylbenzamidines are heated with an excess of sulfur dichloride, 2,4-diphenyl-1,3,5-thiadiazole is formed.The reaction of N-chloro-N'-benzoylbenzamidine with thionyl chloride gives N-(N'- benzoylbenzimidoyl)sulfinylamine, which decomposes with the formation of 1,3,5-triphenyl-sym-triazine when heated in inert solvents.

N2-(ARYLSULFONYL)ARYLAMIDINES. SYNTHESIS AND PROPERTIES OF N2-(ARYLSULFONYL)ARYLAMIDINES AND THEIR N1-ACYL DERIVATIVES

The reaction of carboxylic acid chlorides with N2-(arylsulfonyl)benzamidines was investigated.Conditions were found for the production of N2-arylsulfonyl-N1-acylbenzamidines and N2-arylsulfonyl-N1,N1-diacylbenzamidines.The hydrolysis and ammonolysis of the compounds were studied, and their IR spectra are discussed.It was established that the reactin of arenesulfonamides with the nitriles of aromatic acids in the presence of the alkaline or acidic catalysts leads to the formation of N2-(arylsulfonyl)amidines.

2-IMIDAZOLINES. VI. STRUCTURAL FACTORS AFFECTING THE REARRANGEMENT RATE OF 4,5-DIAMINO-2-IMIDAZOLINES TO N-(1,2-DIAMINOETHYLIDENE)AMIDINES

Several 4,5-diamino-4,5-dihydroimidazoles, 1, have been synthesized in order to study the effects of the substituents in the imidazole ring on the rearrangement to N-(1,2-diaminoethylidene)amidine, 2.The rate of the process increases with the increase in