Ethanol → HCID 67440419, compound

Participants

Reaction Conditions

Reaction Steps

4.42 g (58 mmol) of thiourea are added to a solution of 5.59 g (29 mmol) of 5-(chloromethyl)-3-phenyl-1H-pyrazole in 200 ml of ethanol. The mixture is stirred at 20° C. for 2 days. Most of the solvent is then removed from the mixture, and 10-20 ml of dichloromethane are added. After brief stirring, the precipitate is filtered off with suction and dried. This gives 6.3 g of a product mixture which is used further without further purification. 4.19 g of this mixture are taken up again in 140 ml of N,N-dimethylformamide. 4.55 g of dried potassium carbonate and 4.74 ml of 1,2-dibromoethane are added to this mixture. The mixture is then stirred at 60° C. for 18 h. The reaction mixture is then carefully stirred into water. The aqueous phase is then decanted off, and ethyl acetate is added to the oily residue. The organic phase is dried over Na2SO4 and concentrated. Purification is carried out by silica gel chromatography (cyclohexane/ethyl acetate). This gives 620 mg of the desired product; log P(HCOOH): 2.46; 1H-NMR (ppm): δ (DMSO-d6)=3.20 (t, 2H), 3.94 (s, 2H), 4.32 (t, 2H), 6.54 (s, 1H), 7.31 (t, 1H), 7.40 (t, 2H), 7.65 (d, 2H).

Provenance & Evidence