Sodium Chloride → HCID 22617097, compound

Participants

Reaction Conditions

Reaction Steps

150 ml of dimethyl sulfoxide was admixed with 3.60 g (about 90 mmoles) of oily sodium hydride (about 60%) at room temperature. After the addition, the mixture was heated over an oil bath to an inside temperature of about 70° C., and stirred as such for about one hour. Then, the reaction mixture was cooled to room temperature, and a solution of 25.1 g (92 m moles) of the previously obtained diethyl-4-nitrobenzyl phosphonate and 10.0 g (48.5 m moles) of 5H-dibenzo[a,d]cycloheptene-5-on in 50 ml of dimethyl sulfoxide was added thereto dropwise. After the dropwise addition, the mixture was stirred at room temperature for 15 minutes, and then further stirred with heating at an inside temperature of 70° to 80° C. for 2 hours over an oil bath. After the end of reaction, the mixture was cooled to room temperature, poured into about 1 l of an aqueous saturated NaCl solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then the solvent was removed therefrom under reduced pressure. The residue was admixed with methanol, and the thus precipitated crystal was recovered therefrom by filtration. The thus obtained crystal was recrystallized from methanol-acetone solvent mixture, whereby 10.94 g of 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene was obtained (yield: 69.3%). The melting point was 151.5°-152.5° C. The elemental analysis as C22H15NO2 was as follows:

Provenance & Evidence