Triethylamine → HCID 21802382, compound

Participants

Reaction Steps

To a stirred solution of 0.40 g (1.3 mmols) of N-[2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-hexyl]formamide in 5mL of methylene chloride under nitrogen was added 0.45 mL (3.26 mmols) of triethylamine. To this mixture was added a slurry of 0.439 g (1.63 mmols) of 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate. which was weighed out under a nitrogen atmosphere, in 5 mL of methylene chloride. The reaction mixture was then allowed to stir at room temperature for 12 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed once with 10% hydrochloric acid, brine, and dried over magnesium sutfate. Removal of solvents gave a crude oil which was purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane) to give 0.20 g (52%) of a clear, colorless oil. 1H-NMR 200 MHz (CDCl3, Me4Si) 0.8 (t, J=5 Hz, CH2 -CH3), 1.0-1.6 (m, 4H, 1.90-2.2 (m, 2H), 4.55 (ABq, J=16.8 Hz, JAB =15 Hz, CH2 -N), 7.2-7.5 (q, 4H, aromatic H), 7.9 (s CH=N), 8.0 ppm (s, CH=N).

Provenance & Evidence