Dabco → HCID 44550981, compound

Participants

Reaction Steps

A mixture of methyl 6-hydroxy-2-naphthoate [J. Med. Chem., 2001, 44, 2869-2878] (156) (5.95 g, 29.4 mmol), DABCO (6.61 g, 58.9 mmol) and dimethylthiocarbamoyl chloride (5.46 g, 44.2 mmol) in dry DMF (40 mL) was stirred at room temperature for 8 h. The precipitated solid was collected, washed with water and dissolved in CH2Cl2. The solution was filtered through a column of silica gel and the product was triturated with i-Pr2O and recrystallised from CH2Cl2/hexane to give methyl 6-{[(dimethylamino)carbothioyl]oxy}-2-naphthoate (157) (7.47 g, 88%) as a white solid: mp 144-147° C.; 1H NMR [(CD3)2SO] δ 8.66 (s, 1H), 8.16 (d, J=9.0 Hz, 1H), 8.03 (d, J=8.7 Hz, 1H), 8.00 (dd, J=−8.6, 1.5 Hz, 1H), 7.70 (d, J=−2.3 Hz, 1H), 7.389 (dd, J=8.9, 2.3 Hz, 1H), 3.93 (s, 3H), 3.40 (s, 3H), 3.38 (s, 3H). Anal. (C15H15NO3S) C, H, N.

Provenance & Evidence