Water → HCID 53994067, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7,8-methylenedioxy-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (130 mg, 0.46 mmol) in CH2Cl2 (5 ml) was added triethylamine (1 mL), DMAP (5 mg) and methylisocyanate (60 mg) and the mixture was stirred at 25° C. for 24 h. The reaction mixture was then poured into a separatory funnel containing water (50 mL) and the product was extracted with CH2Cl2 (3×40 mL). The combined extracts were dried over Na2SO4 and solvent removed in vacuo. Purification of the residue by chromatography (1:1 of ethyl acetate: hexane) resulted in the product as a white solid (92 mg, 59%), mp, 180°-182.5° C. 1H NMR (CDCl3) 8.60 (bs, 1H), 7.74 (m, 2H), 7.46 (m, 3H), 6.88 (s, 1H), 6.67 (s, 1H), 6.07 (bs, 1H), 6.03 (bs, 1H), 3.54 (s, 1H) 3.54 (s, 1H), 2.93 (s, 1.5H), 2.92 (s, 1.5H).

Provenance & Evidence