4-Benzyloxybenzoylchloride → HCID 59533951, compound

Participants

Reaction Steps

(Z)-N′-Hydroxy-4-(pyridin-4-yloxy)benzamidine (20 mg, 88 μmol) and 4-benzyloxybenzoyl chloride (28 mg, 114 μmol) were suspended in pyridine (5.0 mL). The solution was refluxed for 21 hours, cooled to room temperature and the solvent was removed under reduced pressure. The solid residue was purified by silica gel column chromatography to give the product as a white solid (10 mg, 27%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.18 (2H, s), 6.55 (2H, d, J=7.8 Hz), 7.14 (2H, d, J=9.0 Hz), 7.36-7.47 (5H, m), 7.50 (2H, d, J=8.6 Hz), 7.68 (2H, d, J=7.8 Hz), 8.17 (2H, d, J=8.8 Hz), 8.33 (2H, d, J=8.6 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 70.5 (CH2), 115.7 (CH), 116.9, 119.5 (CH), 123.1 (CH), 127.6, 127.7 (CH), 128.6 (CH), 129.0 (CH), 129.7 (CH), 130.4 (CH), 136.1, 138.8 (CH), 145.1, 162.7, 167.7, 176.2, 179.3. MS (FAB+): 422 (MH+). HRMS for C26H19N3O3 (MH+): calculated: 422.1505; found 422.1494.

Provenance & Evidence