Dimethyl Sulfoxide → HCID 67269934, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL three-necked flask under an argon atmosphere, cool to −65° C., a solution of 0.65 mL of oxalyl chloride in 5 mL of dichloromethane, then add, dropwise, 0.94 mL of dimethylsulphoxide on 3A molecular sieve. Stir for 10 minutes, then add, dropwise, a solution of 1.65 g of trifluoroacetate of 4-(4,5-dihydro-1H-imidazol-2-yl)-fluoren-9-one acid in 15 mL of dichloromethane then 5 mL of triethylamine. Stir at −65° C. for one hour, then leave to return to room temperature and stir for 2 hours. Pour the reaction mixture into water, and extract with dichloromethane. Wash the organic phases with a saturated aqueous solution of sodium chloride, dry over magnesium sulphate and evaporate to dryness at reduced pressure. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (98/2 by volume), we obtain 560 mg of 4-(1H-imidazol-2-yl)-fluoren-9-one in the form of a yellow powder to be used as it is in the next stage, and having the following characteristics:

Provenance & Evidence