Hydrochloric Acid → HCID 21445649, compound

Participants

Reaction Steps

To a stirred slurry of 1.15 g. (0.030 mole) of lithium aluminum hydride in 80 ml. of dry tetrahydrofuran is added 5.00 g. (0.0203 mole) of 3'-(2,3,5,6-tetrahydroimidazo[2,1-b]thiazol-6-yl)formanilide (Example 12) at a rate sufficient to keep the temperature at 40°-45° C. The reaction mixture is then stirred at room temperature for 3 hours and at 40°-50° C. for 30 minutes. After cooling the reaction, 1.8 ml. of water is cautiously added dropwise and then 2 ml. of 15% aqueous sodium hydroxide. The mixture is filtered and the filter cake washed with tetrahydrofuran. Evaporation of the solvent gives an oil which is dissolved in methanol and acidified with 2-propanolic hydrogen chloride. Filtration of the precipitate gives 4.18 g. (67% yield) of crude product which is recrystallized from methanol and has melting point 229°-231° C. Anal. Calcd. for C12H16N3SCl: C, 47.06; H, 5.60; N, 13.72; S, 10.47; Cl, 23.15. Found: C, 46.82; H, 5.56; N, 13.60; S, 10.40 ; Cl, 23.16.

Provenance & Evidence