Sodium Hydroxide → HCID 178439631, compound

Participants

Reaction Conditions

Reaction Steps

3-Trifluoromethylthiophenol (0.298 g; 1.67 mmol) is dissolved in 20 ml of anhydrous DMF and cooled to 0° C. under a nitrogen atmosphere, and NaH (60% dispersion in mineral oil; 0.0393 g; 1.638 mmol) is added in small portions. The reaction mixture is stirred at 0° C. for 15 min and then at 20° C. for a further 1.5 h, and 0.293 g (0.80 mmol) of 1-(N,N-dimethylsulphamoyl)-2-tert-butyldimethylsilyl-5-(2-chloropropyl) imidazole dissolved in 5 ml of DMF and 10 mg of n-Bu4NI are added and the mixture is heated at 80° C. for 3 days. The solvent is driven off under reduced pressure to yield a brown oil, which is treated with 100 ml of water and extracted 3 times with 40 ml of dichloromethane. The extracts are dried (MgSO4) and concentrated, and the oil obtained is subjected to column chromatography using 2:1 and 1:1 petroleum spirit/ethyl acetate, then dissolved in 10 ml of 2M HCl and heated at 100° C. under reflux for 3 hours. The reaction mixture is then alkalized by adding 10% NaOH (pH approximately 11) and is extracted 3 times with 40 ml of dichloromethane. The extracts are dried (MgSO4) and evaporated to form a clear oil, which is subjected to column chromatography with ethyl acetate as eluent and converted to the oxalate of the desired product in 2-propanol, m.p. 166-168° C.

Provenance & Evidence