[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:11][CH:12]=[CH:13][N:14]=1)([O-:3])=[O:2].[H-].[Na+].N#N.[CH3:19]I>O.O1CCCC1.CN(C)C=O>[CH3:19][N:14]1[CH:13]=[CH:12][N:11]=[C:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]
Under N2, 9.5 g of 2-(2-nitrophenyl)-1H-imidazole in a solution of 100 ml dimethylformamide and 25 ml of anhydrous tetrahydrofuran cooled to 0°-5° C., was treated with 2.3 g of a 50% mineral oil dispersion of NaH. After the N2 evolution ceased, 8.5 g of CH3I was added dropwise over a period of 15 minutes maintaining the temperature at 0°-5°. The reaction mixture was allowed to warm to ambient temperature and then stirred for two hours. The reaction mixture was then poured into water. The aqueous suspension of the product was extracted several times with CH2Cl2. The extracts were combined and dried with anhydrous Na2SO4. The solvent was removed on a rotary evaporator. The last traces of dimethylformamide were removed under high vacuum; a waxy solid remained. The crude product was crystallized from CH3CN. Two crops totaling 3.6 g were obtained. The m.p. was 89°-90°.
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