ChemicalBook CAS DataBase List 1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE

1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE synthesis

10synthesis methods

Product Name:1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE
CAS Number:66121-69-5
Molecular formula:C5H5N3
Molecular Weight:107.11

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Yield:66121-69-5 86%

Reaction Conditions:

Stage #1:1H-imidazole-4-carbonitrile with sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 25; for 1 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide;mineral oil at 25; for 2 h;

Steps:

Step 1: 1-Methylimidazole-4-carbonitrile (lnt-79)
lH-Imidazole-4-carbonitrile (Int-78) (4.000 g, 43 mmol) was dissolved in DMF (80 mL), the solution was cooled to 0 °C, and sodium hydride (60% dispersion in mineral oil, 1.89 g, 47.3 mmol) was added at 0 °C. The mixture was stirred at 25 °C for 1 h. Then, iodomethane (9.30 g, 65.5 mmol) was added. The mixture was stirred at 25 °C for 2 h. After that, water (100 mL) was added, the mixture was extracted with dichloromethane / methanol (10: 1 (v/v), 3 x 100 mL), the combined organic layers were concentrated in vacuo. The crude product was purified by column chromatography (240 g, silica gel, petroleum ether / ethyl acetate, gradient, 91:9 to 33:66 (v/v)) to give the title compound as a white solid (3.95 g, 36.9 mmol, 86% yield).

References:

F. HOFFMANN-LA ROCHE AG;HOFFMANN-LA ROCHE INC. WO2021/110574, 2021, A1 Location in patent:Page/Page column 62-63

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