N-methoxy-N,1-dimethyl-1H-imidazole-4-carboxamide synthesis
- Product Name:N-methoxy-N,1-dimethyl-1H-imidazole-4-carboxamide
- CAS Number:873221-68-2
- Molecular formula:C7H11N3O2
- Molecular Weight:169.18
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Yield:873221-68-2 64%
Reaction Conditions:
with benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;triethylamine in N,N-dimethyl-formamide at 20;
Steps:
42.1 1)
1) N-Methoxy-N-methyl-1-methyl-1H-imidazole-4-carboxamide 1-Methyl-1H-imidazole-4-carboxylic acid (1.26 g), N,O-dimethylhydroxylamine hydrochloride (1.17 g), 1-hydroxybenzotriazole (1.84 g), triethylamine (2.09 mL), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g) were dissolved in N,N-dimethylformamide (50 mL), and the solution was stirred overnight at room temperature. The reaction solvent was evaporated under reduced pressure, and ethanol was added to the residue. Insoluble matter was removed through filtration, and the solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform - methanol - water, lower phase), to thereby give N-methoxy-N-methyl-1-methyl-1H-imidazole-4-carboxamide as a solid product (1.08 g, 64%). 1H-NMR(400MHz,CDCl3)δ:3.45(3H,s), 3.73(3H,s), 3.78(3H,s), 7.45(1H,s),7.54(1H,s).
References:
EP1762568,2007,A1 Location in patent:Page/Page column 58