Butyl 4-aminobenzoate → 4-[3-(Naphthalene-2-carbonyl)-thioureido]-benzoic acid butyl ester

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Reaction Steps

2-Naphthoyl chloride (190 mg, 1 mmol) is added to a solution of ammonium thiocyanate (200 mg, about 3 mmol) in acetone (5 ml) and stirred at room temperature for 1 hour. Butyl 4-aminobenzoate (180 mg, 0.93 mmol) is added to the reaction mixture. Stirring is continued overnight at room temperature. The solid, which forms is filtered and washed with water (2×5 ml) followed by acetone/hexane (3:1) (2×10 ml) and dried. The product (140 mg) is characterized by NMR (Bruker, 300 MHz) and MS. 1H NMR (300 MHz, CDCl3) δ (Ppm): 12.9 (s, 1H), 9.27 (1H), 8.43 (s, 1H), 8.11 (d, 2H, J=6.0), 7.99 (d, 2H, J=6.0), 7.91 (m, 4H), 7.65 (m, 2H), 4.34 (t, 2H, J=6.6 Hz), 1.81-1.72 (m, 2H), 1.55-1.43 (m, 2H), 0.99 (t, 3H, J=7.3 Hz). MS (APCI) m/z 407 [M+H]+.

Provenance & Evidence