158365-99-2

Usage

Chemical Properties

Brown SolidLight Brown Solid

Synthesis Reference(s)

The Journal of Organic Chemistry, 64, p. 8084, 1999 DOI: 10.1021/jo9824910

InChI:InChI=1/C7H11ClN2/c1-2-3-4-7-9-5-6(8)10-7/h5H,2-4H2,1H3,(H,9,10)

Upstream product

• 110-59-8 pentanonitrile 
• 57246-71-6 methyl pentanimidate 
• 999-09-7 ethyl valerimidate 
• 109-51-3 pentanimidamide 
• 36801-39-5 N-(cyanomethyl)pentanamide 
• 154147-42-9 2-butyl-2-imidazolin-5-one 

Downstream Products

• 83857-96-9 2-n-butyl-5-Chloroimidazole-4-Carbaldehyde 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 

Relevant academic research and scientific papers

Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan

Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl3/ DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl3/DMF allowed development of several closely related syntheses of aldehyde 2.

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.

2-substituted 5-chlorimidazoles

The 2-substituted 5-chlorimidazoles of general formula: STR1 are new intermediate products for the production of antihypertensive pharmaceutical agents or of herbicidal compounds. A process for the production of these intermediate products as well as a new process for the further reaction of 2-substituted 5-chlorimidazoles of general formula I, wherein R1 is hydrogen, to the 2-substituted 5-chlorimidazole-4-carbaldehydes of general formula: STR2