775303-48-5

Upstream product

• 5259-69-8 1-(hydroxyamino)cyclohexanecarbonitrile 
• 54255-11-7 2-chloro-4,5-dihydro-1H-imidazole 

Downstream Products

• 62492-26-6 1-(1,3-benzothiazol-2-yl)imidazolidin-2-one 
• 775303-51-0 1-({[(2-oxoimidazolidin-1-yl)carbonothioyl]thio}amino)cyclohexanecarbonitrile 

Relevant academic research and scientific papers

First stable O-amidinylhydroxylamines and their transformations into sulfenamides by intramolecular 1,5-O→S amine migration

The reaction of 2-chloro-4,5-dihydroimidazole (1) with aliphatic hydroxylamines 2-4 gives O-amidinylhydroxylamines 5-7 in contrast to the analogous reaction of 1 with N-arylhydroxylamines in which N-substitution occurs. A number of thiocarbamoylsulfenamides 8-10 have been prepared by the reaction of 5-7 with carbon disulfide under basic and mild conditions. The key step in the 1,5-O→S amine migration involves the tandem nucleophilic addition-electrophilic amination reaction. The intermolecular version of this process using preformed triethylammonium dithiocarbamates gives the corresponding sulfenamides 14-16. Functionalized ethylenediamines 17-19 are obtained by treatment of 8 and 9 with amines. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.