Hydrochloric Acid → Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate

Participants

Reaction Steps

3-Ethyl-5-(1-methyl-1H-tetraazol-5-yl)aniline (3.83 g, 19 mmol, 1 equiv.), was dissolved in THF at 25° C. under nitrogen then 2,6-lutidine (Aldrich, 2.17 ml, 19 mmol, 1 equiv.) was added. Cooled the reaction to 0° C. Added a THF solution of phenyl chloroformate (2.36 ml, 19 mmol, 1 equiv.) dropwise via an addition funnel. Worked up after 1 hour by adding ethyl acetate and 0.1 N HCl. Separated the layers and rinsed the organic layer twice more with 0.1 N HCl and once with brine. The organic layer was dried over MgSO4 then stripped in vacuo to give 6.00 g of tan solids as product. NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.50-7.30 (m, 5H), 7.30-7.10 (m, 3H), 4.17 (s, 3H), 2.71 (q, 2H, J=7 Hz), 1.27 (t, 3H, J=7 Hz).

Provenance & Evidence