Water → Methyl 4-(5-hexanamidobenzo[b]thien-3-ylmethyl)-3methoxybenzoate

Participants

Reaction Steps

Hexanoyl chloride (0.024 g.) was added to a stirred solution of methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate (H) (0.06 g.), and N-methylmorpholine (0.1 ml.) in dichloromethane (3 ml.). The mixture was stirred for 1 hour and then poured into water (20 ml.). The aqueous mixture was extracted with dichloromethane (2×20 ml.). The combined extracts were dried (MgSO4), and evaporated. The mixture was recrystallized from a mixture of ethyl acetate and hexane to give the title compound (0.05 g., 75%) as a colorless solid: NMR (250 MHz, DMSO-d6): 0.87 (t,3 H, CH2CH3), 1.28 (m,4 , CH2.CH2.CH3), 1.59 (quintet,2 H, CH2CH2CON), 2.29 (t,2 H, CH2CON), 3.84 (s, 3 H, OCH3), 3.91 (s,3 H, OCH3), 4.11 (s,2 H, CH 2 --Ar), 7.14 (d,1 H), 7.34 (s,1 H), 7.49 (m,3 H), 7.86 (d,1 H), 8.11 (d, 1 H), 9.95 (s,1 H).

Provenance & Evidence