1-(1H-IMIDAZOL-2-YL)-ETHANONE HCL synthesis
- Product Name:1-(1H-IMIDAZOL-2-YL)-ETHANONE HCL
- CAS Number:53981-69-4
- Molecular formula:C5H6N2O
- Molecular Weight:110.11
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Yield: 69%
Reaction Conditions:
Stage #1:1-(diethoxymethyl)-1H-imidazole with n-butyllithium in tetrahydrofuran;hexane at -55 - -35; for 0.25 h;
Stage #2:N,N-dimethyl acetamide in tetrahydrofuran;hexane at 20; for 25.5833 h;
Steps:
43.1
1) 1-(1H-Imidazol-2-yl)-1-ethanone n-Butyllithium (a 1.58 M solution in hexane, 25.3 mL) was added dropwise to a solution of 1-diethoxymethyl-1H-imidazole (6.80 g) in tetrahydrofuran (100 mL) for 5 minutes under cooling to -55°C, while maintaining the internal temperature at -35°C or lower, and the resultant mixture was stirred for 15 minutes at an internal temperature of -40°C. N, N-Dimethylacetamide (5.57 mL) was added dropwise to the reaction solution for 5 minutes, and the mixture was stirred for 25.5 hours at room temperature. Diethyl ether and an aqueous 0.1 N hydrochloric acid solution were added to the reaction solution, and the mixture was partitioned. The aqueous layer was neutralized with sodium hydrogen carbonate, and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. After separation by filtration, the solvent was evaporated under reduced pressure, and 1-(1H-imidazol-2-yl)-1-ethanone (3.06 g, 69%) was obtained as a solid. 1H-NMR(400MHz, CD3OD)δ: 2.56(3H, s), 7.27(2H, br s). ESI-MSm/z: 111(M+H)+.
References:
DAIICHI PHARMACEUTICAL CO., LTD. EP1785418, 2007, A1 Location in patent:Page/Page column 60-61
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