1349129-34-5

Basic information

• Product Name: 1-benzyl-5-methyl-1H-imidazole-4-carbohydrazide 3-oxide
• Synonyms: 1-benzyl-5-methyl-1H-imidazole-4-carbohydrazide 3-oxide
• CAS NO: 1349129-34-5
• Molecular Weight: 246.269
• Mol File: 1349129-34-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-benzyl-5-methyl-1H-imidazole-4-carbohydrazide 3-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-methyl-1H-imidazole-4-carbohydrazide 3-oxide(1349129-34-5)
• EPA Substance Registry System: 1-benzyl-5-methyl-1H-imidazole-4-carbohydrazide 3-oxide(1349129-34-5)

Safety Data

• Hazardous Substances Data: 1349129-34-5(Hazardous Substances Data)

Upstream product

• 4393-14-0 N-methylenebenzylamine 
• 100-46-9 benzylamine 
• 1100817-31-9 C₁₄H₁₆N₂O₃ 

Downstream Products

• 1349129-59-4 1-benzyl-5-methyl-N'-(tricyclo[3.3.1.1(3,7)]dec-2-ylidene)-1H-imidazole-4-carbohydrazide 3-oxide 
• 1349129-87-8 5-(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)-2,4-dihydro-4-methyl-3H-1,2,4-triazole-3-thione 
• 1349129-88-9 5-(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)-N-methyl-1,3,4-thiadiazol-2-amine 
• 1349129-84-5 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-methylhydrazinecarbothioamide 
• 1370588-25-2 5-(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)-2,4-dihydro-4-phenyl-3H-1,2,4-triazole-3-thione 
• 1370588-33-2 4-{[5-(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)-1,3,4-thiadiazol-2-yl]amino}benzenesulfonic acid 
• 1370588-34-3 5-(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)-N-butyl-1,3,4-thiadiazol-2-amine 
• 1370588-18-3 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-(tert-butyl)hydrazinecarbothioamide 
• 1370588-41-2 4-[(2-acetylhydrazinyl)carbonyl]-1-benzyl-5-methyl-1H-imidazol-1-ium 3-oxide 
• 1370588-16-1 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-phenylhydrazinecarbothioamide 
• 1370588-17-2 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-butylhydrazinecarbothioamide 
• 1370588-37-6 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-butylhydrazinecarboxamide 
• 1449684-38-1 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-39-2 2-[ (1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-phenylhydrazinecarboselenoamide 

Relevant articles and documents

Synthesis and evaluation of antimicrobial activity of hydrazones derived from 3-oxido-1H-imidazole-4-carbohydrazides

In this work we reported the synthesis and evaluation of in vitro antimicrobial activities of hydrazones 6 obtained from 3-oxido-1H-imidazole-4- carbohydrazides 4. All new compounds were characterized by spectroscopic methods. Hydrazones 6 were tested for their in vitro antimicrobial activity against four Gram-positive and four Gram-negative strains of bacteria as well as one fungal species. Three of the tested compounds appeared to be promising agents against reference strains of Escherichia coli, Staphylococcus aureus and Staphylococcus epidermidis. They were also tested against twelve clinical isolates of S. aureus and their cytotoxic effect on murine fibroblasts and HeLa human tumor cell line was determined.

Synthesis and selected reactions of hydrazides containing an imidazole moiety

The preparation of two types of imidazole derivatives bearing a hydrazide group was achieved by treatment of the corresponding esters with NH 2NH2·H2O in MeOH at room temperature. In the case of 4-(ethoxycarbonyl)-1H-imidazole 3-oxides 3, hydrazides of type 1 were formed with retention of the N-oxide structure (Scheme 1). Interestingly, due to a strong H-bonding, no deoxygenation of the N→O function could be achieved even by treatment of 3 with Raney-Ni. The second type, 2-[(1H-imidazol-2-yl)sulfanyl]acetohydrazides 2, was obtained from 1H-imidazole-2(3H)-thiones 4 in two steps via S-alkylation with methyl bromoacetate, followed by treatment with NH2NH2· H2O (Scheme 2). An imidazole 7, containing both types of hydrazide groups, was prepared analogously from ethyl 2,3-dihydro-2-thioxo-1H-imidazole-4- carboxylate 4d (Scheme 4). Both types of hydrazides, 1 and 2, were transformed successfully to the corresponding acylhydrazones 8 and 9, respectively (Scheme 5). Furthermore, it has been shown that hydrazides of type 1 are useful starting materials for the synthesis of 1,2,4-triazole-3-thiones 11 and 1,3,4-thiadiazole-2-amines 12, bearing an imidazole 3-oxide moiety (Scheme 7). Copyright