Furosemide → HCID 58979751, compound

Participants

Reaction Steps

A mixture of furosemide (ONBIO Inc., 20 g, 60.5 mmol), K2CO3 (8.3 g, 60.5 mmol) and ethyl bromoacetate (10.1 g, 6.7 mL, 60.5 mmol) in dry acetone (400 mL) was stirred at room temperature for 16 hours. The solvent was evaporated at reduced pressure. The residue was diluted with CH2Cl2, the solid K2CO3 was removed by filtration. The filtrate was washed with water, brine and dried over Na2SO4. The residue obtained after evaporation of the solvent was dried under vacuum to give the title compound (23.5 g, 93% yield) as a white foam. Mp 46° C. 1H NMR (300 MHz, d6-DMSO) δ 8.48 (s, 1H), 8.37 (br t, J=5.6 Hz, 1H), 7.62 (s, 1H), 7.39 (br s, 2H), 7.14 (s, 1H), 6.37-6.43 (m, 2H), 4.93 (s, 2H), 4.62 (br d, J=5.7 Hz, 2H), 4.17 (q, J=7.0 Hz, 2H), 1.19 (br t, J=14.1 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) δ 167.6, 165.8, 152.2, 151.1, 142.8, 137.0, 133.0, 127.1, 114.1, 110.5, 107.7, 106.3, 61.2, 61.0, 14.0. Mass spectrum (API-TIS) m/z 417 (MH+), 434 (MNH4+). Anal. calcd for C16H17ClN2O7S: C, 46.10; H, 4.11; N, 6.72. Found: C, 46.13; H, 3.97; N, 6.47.

Provenance & Evidence