Triethylamine → HCID 46932515, compound

Participants

Reaction Steps

Oxalyl chloride (0.934 g, 3.92 mmol) followed by N,N-dimethylformide (0.1 mL) was added dropwise to a suspension of 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (0.60 g, 1.71 mmol) in dichloromethane (30 mL) and the mixture was stirred at ambient temperature for 8 hour. After this time, TLC analysis showed no acid remaining so the mixture was allowed to be concentrated in vacuo to give a yellow solid. The resulting acid chloride solid was dissolved in dry tetrahydrofuran (10 mL). 2-(methylthio)ethanamine (0.047 g, 0.52 mmol) followed by triethylamine (0.066 g, 0.65 mmol) was added to a 2.5 mL aliquot of acid chloride solution in tetrahydrofuran at 0° C. The resulting mixture was stirred at ambient temperature for 3 hours. TLC analysis showed no acid chloride remaining so the mixture was diluted with ethylacetate and washed with water and brine. The organic layer was separated, dried (Na2SO4), filtered and the solvent was removed to afford a brown oil. The crude material was purified by silica gel chromatography using an 85:15 mixture of hexane and ethyl acetate as eluent to afford the title product as a brown solid (55 mg, 13% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.99 (1H, m), 8.98 (2H, m), 8.41 (1H, s), 3.39 (2H, m), 2.59 (2H, m), 2.08 (3H, s). MS m/z: 422.20, 424.21 [M+H]+.

Provenance & Evidence