213134-29-3

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 103-71-9 phenyl isocyanate 
• 74-88-4 methyl iodide 
• 100-61-8 N-methylaniline 
• 92289-43-5 imidazole-1-carboxylic acid methylphenylamide 

Downstream Products

• 1143514-93-5 (±)-N-methyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamide 

Relevant academic research and scientific papers

α-arylation of cyclic amines by aryl transfer in lithiated ureas

Treatment with base of N′-aryl urea derivatives of hetero-or carbocyclic amines with benzylic nitrogen atoms promotes rearrangement with transfer of the aryl ring from N to C, giving rise to α-arylated products. Georg Thieme Verlag Stuttgart.

Carbamoylimidazolium and thiocarbamoylimidazolium salts: Novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides

Carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N,N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the 'imidazolium' effect. Kinetic studies on the base promoted hydrolysis of both carbamoylimidazoles and carbamoylimidazolium salts reveal over a hundred-fold rate acceleration. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively. Analogous thiocarbamoylimidazolium salts were also synthesized from secondary amines and N,N′-thiocarbonyldiimidazole (TCDI), followed by methylation with iodomethane.

An efficient new protocol for the formation of unsymmetrical Tri-and tetrasubstituted ureas

A new method for producing unsymmetrical, tetrasubstituted ureas from N, N'carbonyldiimidazole (CDI) is presented. Carbamoyl imidazolium salts are prepared from the reaction of CDI with a secondary amine, followed by alkylation with MeI. Secondary amines add with ease to imidazolium salts at room temperature to give unsymmetrical, tetrasubstituted ureas in excellent yields.