Sodium Hydroxide → (11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

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Reaction Steps

To a stirred solution of 1-benzoyl-3-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 8, 0.6 g, 1.54 mmol) in 10 mL of tetrahydrofuran was added 1.8 mL of 2.0 N aqueous sodium hydroxide. The mixture was heated to reflux for 3 hrs, diluted with water (10 mL) and extracted with ethyl acetate (3×100 mL). The combined organic fractions were dried with magnesium sulfate and concentrated under reduced pressure. The solid was washed with 1:1 ethyl acetate/hexanes (50 mL) to give a solid (yield 397 mg, 90.3%). H1 NMR (methanol d4) δ: 9.83 (s, 1H), 9.50 (s, 1H), 7.81 (s, 1H), 7.55-7.54 (d, 1H, J=1.9), 7.32-7.30 (m, 2H), 6.96-6.86 (m, 5H), 5.72 (s, 1H), MS (ES): MH+ 285.1.

Provenance & Evidence