Disilathiane, 1,1,1,3,3,3-hexamethyl- → 3-(7-chloro-8-dimethylamino-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-thiobenzamide

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Reaction Steps

The title compound was prepared from 3-(7-chloro-8-dimethylamino-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-thiobenzamide {prepared from 3-(7-chloro-8-dimethylamino-4-oxo-4,5-dihydro-3H-benzo[b][1,4] diazepin-2-yl)-benzonitrile (Example 1) as follows: To a solution of hexamethyldisilthiane (0.55 mL, 2.6 mmol) in 1,3-dimethyl-2-imidazolidinone (2.6 mL) was added at 20° C. sodium methoxide (0.13 g, 2.5 mmol). The mixture was stirred for 15 min. and the blue solution formed was then added to a solution of 3-(7-chloro-8-dimethylamino-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile (Example 1) (0.34 g, 1.0 mmol) in 1,3-dimethyl-2-imidazolidinone (2 mL). The mixture was stirred for 3 h at 20° C. and then poured into water. The precipitate was isolated by filtration and triturated with acetone to give 3-(7-chloro-8-dimethylamino-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-thiobenzamide (0.35 g) as yellow solid, mp 234° C. dec.MS (ISP) 373.2 [(M+H)+].} (0.71 g, 1.9 mmol), 1,3-dichloro-2-propanone (0.36 g, 2.85 mmol) and sodium bicarbonate (0.24 g, 2.85 mmol) in 1,4-dioxane (15 mL) was heated to 60° C. for 48 h. The clear solution was evaporated in vacuum. The a solution of the residue in 1,4-dioxane (5 mL) was added 2N KOH (3.8 mL) and the mixture was stirred at 20° C. for 1 h. Water (100 mL) was added and the mixture was stirred for 0.5 h.

Provenance & Evidence