Methanol → 2-Benzyl-1-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-isothiourea

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Reaction Steps

To a solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 50 mg, 0.18 mmol) in DMF (1 mL) was added benzyl bromide (21 μL, 0.18 mmol). The solution was stirred at room temperature for 2 hr then heated at 60° C. for 1 hr. The solvent was removed under vacuo. The residue was dissolved in a mixture of tetrahydrofuran (5 mL) and diethyl ether (5 mL) and treated with 2 mL of saturated sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulfate and evaporated to give an oily residue which was subjected to silica gel column chromatography (98% dichloromethane: 2% methanol). H1 NMR (acetone d6) δ: 8.91 (bs, 1H), 7.42-7.21 (m, 5H), 7.09-6.89 (m, 7H), 5.93 (bs, 1H), 4.31 (s, 2H).

Provenance & Evidence