67221-91-4

Upstream product

• 100-46-9 benzylamine 
• 98-88-4 benzoyl chloride 
• 6926-50-7 1-benzyl-1H-tetrazole 
• 506-68-3 bromocyane 
• 1485-70-7 N-benzylbenzamide 

Downstream Products

• 1404074-02-7 N-benzoyl-N’-benzyl-S-phenylisothiourea 
• 1404074-02-7 C₂₁H₁₈N₂OS 
• 1404074-03-8 N-benzoyl-N’-benzyl-S-(4-methyl)phenylisothiourea 
• 1404074-03-8 C₂₂H₂₀N₂OS 
• 93870-87-2 N-(1-benzyltetrahydropyrimidin-2(1H)-ylidene)benzamide 
• 16565-12-1 N-benzoyl-N’,N”-dibenzylguanidine 

Relevant academic research and scientific papers

Cyanide-Free Synthesis of Air Stable N-Substituted Li and K Cyanamide Salts from Tetrazoles. Applications toward the Synthesis of Primary and Secondary Cyanamides as Precursors to Amidines

A practical two-step synthesis of N,N′-disubstituted cyanamides consists in the low-temperature metalation of N-substituted 5H-tetrazoles that undergo spontaneous cycloreversion at 0 °C releasing dinitrogen, and forming N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Remarkably, the N-substituted Li and K cyanamides are air stable white solids at room temperature. Addition of lithium organometallics to the N,N′-disubstituted cyanamides provides a new method for accessing N,N′-disubstituted amidines.

Rearrangements of N-acyl isothioureas. alternate access to acylguanidines from cyanamides

We report a tin-free one-pot radical approach to the synthesis of N-acyl isothioureas and acylguanidines from N-acyl cyanamides. Photoactivated reduction of aromatic disulfides in the presence of Huenig's base results in hydrothiolation of the cyanamide moiety, followed by spontaneous 1,3-migration of the acyl group. Onward reaction of the isothioureas obtained with amines led to the corresponding N-acylguanidines, where the acyl group is attached to the nitrogen atom formerly at the cyano-end of the starting material.