Methyl iodide → HCID 14625407, compound

Participants

Reaction Steps

To a mixture of 2,3,4,5-tetrahydro-3-phenyl-1H-[1,2,5]triazepino[1,2-a][1,2,4]benzotriazine-7(8H)-thione (3.1 g from Example 12) and potassium t-butoxide (1.29 g) in N,N-dimethylformamide (50 ml, dried over 4A molecular sieves) was added methyl iodide (2 ml) and the reaction flask was sealed rapidly. An exothermic reaction ensued. The solution was left at room temperature overnight. The solution was evaporated and the residue was extracted with chloroform. The extract was applied to a column (71×3.2 cm) of dry column grade neutral alumina prepacked in chloroform. Elution with chloroform furnished a major component. Appropriate fractions were evaporated to a syrup. Trituration with heptane gave crude titled product; wt. 2.21 g, (65%), mp=125°-127°. Recrystallization (with decolorization) from dichloromethane-heptane furnished pure product; mp=128°-130°, m/e (E.I.) 324; maxKBr 1589, 765, 748, 693 cm-1 ; pmr (100 MHz, DMSO-D6) 2.42 (3H, singlet), 3.29 (2H, triplet, J=6 Hz), 3.67 (2H, triplet, J=6 Hz), 3.81 (2H, triplet, J=6 Hz), 3.89 (2H, triplet, J=6 Hz), 6.64-7.34 (9H, overlapping multiplets).

Provenance & Evidence