Hydrochloric Acid → [(4-Dimethylaminophenyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 175.0 ml of ethyl alcohol, 27.5 ml of concentrated hydrochloric acid, 30.4 g (0.15 mole) of 86.4 percent sodium p-toluenesulfinate and 18.5 g (0.125 mole) of p-dimethylaminobenzaldehyde chilled to approximately 5° C., there was slowly added 19.5 g (0.113 mole) of 91.2 percent 1-ethyl-2-methylindole. The resulting mixture was stirred for approximately three and one half hours at ambient temperature, during which period the color changed from blue to yellow. The pH of the mixture was adjusted to approximately 8 by the addition of 40.0 g of triethanolamine and, after stirring approximately twenty minutes at room temperature, the temperature was raised to and maintained at 55°-60° C. for approximately twenty minutes. After cooling to approximately 10° C., the separated pink solid was collected by filtration and washed with 100.0 ml of cold ethyl alcohol. The solid was then suspended in a mixture of 350.0 ml of water and 10.0 g of triethanolamine at ambient temperature for approximately thirty minutes, collected by filtration and washed first with 150.0 ml of 3 percent aqueous triethanolamine and finally with 150.0 ml of water. After drying in vacuo at 40° C., there was obtained 42.2 g of [(4-dimethylaminophenyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane (Formula II: R=4--CH3 ; R1 =C2H5 ; R2 =CH3 ; R3 =R5 =H; R6 =N(CH3)2) which softened at 155° C. and melted at 159°-161° C.

Provenance & Evidence