Water → HCID 22921534, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 1.3 grams (0.003 mole) of a tautomeric mixture of 1-methyl-3-(2-trifluoromethylbenzimidazol-5-yl)-6-trifluoromethyluracil and 1-methyl-3-(2-trifluoromethylbenzimidazol-6-yl)-6-trifluoromethyluracil (prepared in Example 4) in 15 mL of N,N-dimethylformamide was stirred, and 0.9 gram (0.007 mole) of potassium carbonate was added. The reaction mixture was then stirred at ambient temperature for one hour, and 0.5 gram (0.004 mole) of 3-bromopropene was added in one portion. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for an additional two hours. The reaction mixture was then poured into water, and the resultant solid precipitate was collected by filtration. The solid was washed with water and then with diethyl ether. Thin layer chromatographic analysis of the solid indicated it to be a 1:1 mixture of the proposed products. The solid was subjected to high pressure liquid chromatography, with 5% 1-methylethanol in hexane as the eluant. The appropriate product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of 1-methyl-3-[1-(2-propen-1-yl)-2-trifluoromethylbenzimidazol-6-yl]-6-trifluoromethyluracil, mp 171°-173° C. (compound 9). Other appropriate product-containing fractions were combined and concentrated under reduced pressure, yielding 0.4 gram of 1-methyl-3-[1-(2-propen-1-yl)-2-trifluoromethylbenzimidazol-5-yl]-6-trifluoromethyluracil, mp 185°-187° C. The NMR spectra were consistent with the proposed structures.

Provenance & Evidence