Tyrosol → HCID 14328859, compound

Participants

Reaction Steps

A solution of 10.0 grams (0.0309 mol) of 3-acetoxy-7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-one and 11.0 grams (0.080 mol) of 4-hydroxyphenethylalcohol (Aldrich) in 50 ml. dry N,N-dimethylformamide was stirred in an ice bath and hydrogen chloride gas was bubbled into the solution for 5-10 minutes. After standing at room temperature for 18 hours, the reaction mixture was poured onto ice and the pH adjusted to 7.5 with ammonium hydroxide. The mixture was filtered and the gummy precipitate was stirred with 50 ml. dichloromethane and 50 ml. water for 5 minutes and filtered. The solid was crystallized from a mixture of dichloromethane and methanol to give 9.6 grams (77%) of the compound of Formula I (a) as white rods, m.p. 222°-230° C.; 1R (KBr) 3310, 3215, 3140, (OH,NH), 1685 cm-1 (C=O); NMR (DMSO-d6) 2.86 (t, 2H, CH2Ar), 3.77, 3.95 (2q, 2H, CH2O), 4.78 (s, 1H, CH), 6.68, 7.09 (2d, 4H, aromatics), 9.18 (s, 1H, OH), 10.81 (s, 1H, NH); mass spectrum m/e 406 (M+ ) Anal. Calcd for C23H19ClN2O3 : C, 67.90; H, 4.71; N, 6.89. Found: C, 67.91; H, 4.83; N, 6.80.

Provenance & Evidence