Sodium Chloride → [(4-Dimethylaminophenyl)(1-ethyl-2-methylindol-3-yl)(2-methylindol-3-yl)]methane

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Reaction Steps

With stirring, 2.0 g of potassium hydroxide was added slowly to a mixture of 6.7 g of [(4-dimethylaminophenyl)(1-ethyl-2-methylindol-3-yl)(4-methylphenylsulfonyl)]methane, 2.5 g of 2-methylindole and 75.0 ml of acetone. The resulting mixture was stirred approximately twenty hours at ambient temperature and slowly added with stirring to cold water. The precipitate which formed was collected by filtration and washed three times each with 50.0 ml of hexane. The hexane-wet filter cake was dissolved in toluene. The toluene solution was extracted with water and the toluene layer containing the product was stirred with decolorizing carbon for approximately thirty minutes and the carbon removed by filtration. The toluene was removed by distillation at reduced pressure to obtain a gum-like residue. The residue was dissolved in 150.0 ml of acetone and the resulting solution was added slowly to a mixture of 800.0 ml of water, 10.0 ml of concentrated ammonium hydroxide and 50.0 ml of saturated aqueous sodium chloride solution. The solid which separated was collected by filtration, washed with water and dried in vacuo to obtain 3.9 g of [(4-dimethylaminophenyl)(1-ethyl-2-methylindol-3-yl)(2-methylindol-3-yl)]methane (Formula V: R1 =R2 =R8 =R9 =R11 =H; R3 =N(CH3)2 ; R7 =R10 =CH3 ; R6 =C2H5), a pale brown-colored solid which melted over the range of 69°-80.5° C. An infrared maxima appeared at 745 (C--H;s) cm-1. A toluene solution of the product spotted on an acidic clay-coated paper or phenolic resin-coated paper slowly developed a blue-red-colored image.

Provenance & Evidence