Benzoyl isothiocyanate → 1-Benzoyl-3-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

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Reaction Steps

A stirred solution of 2-amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one (Example 6, 0.5 g, 2.22 mmol) in 20 mL of THF was cooled to 0° C. (ice/water bath). Benzoyl isothiocyanate was added dropwise over a period of 10 min. The mixture was warmed to room temperature and stirred for 20 hr. The solvent was evaporated and the yellow solid washed with 50 mL of 1:1 ethyl acetate/hexanes solution (yield 0.736 g, 85%). H1 NMR (DMSO d6) δ: 12.43 (s, 1H), 11.53 (s, 1H), 9.92 (s, 1H), 8.00-7.95 (m, 3H), 7.06-6.96 (m, 6H), MS (ES): MH+ 389.1.

Provenance & Evidence