679412-75-0

Usage

Chemical Properties

White Solid

InChI:InChI=1/C15H20N2O2/c1-2-3-9-15(18)17-14(10-16)12-19-11-13-7-5-4-6-8-13/h4-8,14H,2-3,9,11-12H2,1H3,(H,17,18)

Upstream product

• 645394-47-4 2-amino-3-benzyloxy-propionitrile 
• 109-52-4 valeric acid 
• 60656-87-3 benzyloxyacetoaldehyde 

Downstream Products

• 79047-41-9 2-n-butyl-4-chloro-5-hydroxymethylimidazole 
• 679412-76-1 5-benzyloxymethyl-2-butyl-4-chloro-1H-imidazole 

Relevant academic research and scientific papers

New method for the synthesis of diversely functionalized imidazoles from N-acylated α-aminonitriles

(Equation presented) A new general method for the synthesis of medicinally important diversely functionalized imidazoles from N-acylated α-aminonitriles has been developed. N-Acylated α-aminonitriles were reacted with triphenylphosphine and carbon tetrahalide to afford 2,4-disubstituted 5-halo-1H-imidazoles in good yield. This new methodology was applied for the synthesis of 2-butyl-4-chloro-5-hydroxymethylimidazole. These halo-imidazoles can be directly converted to 2,4,5-trisubstituted imidazoles through palladium-catalyzed coupling reactions.

Process for preparing 2,4,5-trisubstituted imidazoles from N-acylated alpha-amino nitriles

The invention is a process for preparing an imidazole of formula I which comprises treating an N-acylated α-amino nitrile with a phosphine and a carbon tetrahalide of the formula CX4, wherein X is Cl or Br, to form a haloimidazole of the formula wherein R1 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2-aryl, and aryl; and R2 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2—O-aryl and aryl; and X is selected from the group consisting of Cl and Br.