Dimethylamine → HCID 23463951, compound

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Reaction Steps

The resulting oil (7.3 g--yield: 61%), which tends to decompose if distillation thereof is attempted, shows by elemental analysis and under NMR spectrum to consist of practically pure 2-benzyl-3-(3-hydroxypropylthio)-indazole. (b) To a solution of 3 g (0.01 mols) of the preceding product in 15 ml of pyridine there is added 1.9 g (0.01 mols) of p-toluenesulfonylchloride. The mixture is left for 3 hours under stirring at room temperature, is then poured into 100 ml of a water-ice mixture and the oil which separates is extracted with ethyl ether. The oil which is obtained by removing the solvent is dissolved in 20 ml of a toluene solution containing 10% (0.044 mols) of dimethylamine and the resulting solution is heated for 16 hours at 120° in a closed test tube. At the end of the heating cycle, the toluene solution is extracted with an equal volume of 2 N HCl and made basic with NaOH. The oil which separates is extracted with ether and to the ether solution there is added gaseous HCl. The hydrochloride which precipitates is removed by filtration and recrystallized from isopropanol-isopropyl ether.

Provenance & Evidence