4-chloro-3,4-dihydro-2H-thiochromene

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 100 ml 3-necked flask equipped with a condenser, addition funnel and magnetic stirring bar and under a nitrogen atmosphere was charged with a solution of homopiperazine (3.0 g; 30.5 mmol) in DMAC (35 ml). Potassium iodide (300 mg) was added followed by the addition of a solution of 4-chloro-3,4-dihydro-2H-benzothiopyran (1.15 g; 6.1 mmol) in DMAC (15 ml). This solution was then heated in an oil bath at 60° C. overnight. The reaction mixture was partitioned between water and ethyl acetate, washed with brine and dried with magnesium sulphate. Filtration and evaporation of solvent gave a yellow oil (1.15 g) which exhibited a satisfactory proton nmr spectrum (300 MHz, CDCl3). This material was used without further purification. A 100 ml 3-necked flask equipped with a condenser, addition funnel and magnetic stirring bar and under a nitrogen atmosphere The reaction mixture was partitioned between water and ethyl acetate washed with brine dried with magnesium sulphate Filtration and evaporation of solvent

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 25 ml 3-necked flask equipped with a condenser and magnetic stirring bar and under a nitrogen atmosphere was charged with a solution of N-methylhomopiperazine (0.35 ml; 2.81 mmol) in DMAC (10 ml). Potassium iodide (0.1 g) was added followed by the addition of 4-chloro-3,4-dihydro-2H-benzothiopyran (0.20 g; 1.2 mmol). This solution was then heated at 60° C. overnight, cooled, and partitioned between water and ethyl acetate which was washed with brine and dried with magnesium sulphate. Filtration and evaporation of solvent gave a yellow oil which was distilled by kugelrohr to give the title compound as an oil (0.31 g), bp (air bath temperature) 130-140° C. at 100 mtorr; essentially homogeneous by tlc (silica gel, 89:10:1 CH2Cl2:CH3OH:NH4OH), Rf 0.46; 1H nmr δ2.37 (s, 3H), 3.82-3.87 (m, 1H), 6.98-7.34 (m, 3H), 7.69-7.71 (d, 1H). A 25 ml 3-necked flask equipped with a condenser and magnetic stirring bar and under a nitrogen atmosphere cooled partitioned between water and ethyl acetate which was washed with brine dried with magnesium sulphate Filtration and evaporation of solvent gave a yellow oil which was distilled by kugelrohr