Diethyl Oxalate → HCID 57565039, compound

Participants

Reaction Steps

Reaction of the adduct of diethyl oxalate (7.26 g, 49.7 mmol), ethyl benzyloxyacetate (9.65 g, 49.7 mmol) and sodium hydride (2.19 g of a 60% dispersion in mineral oil, 54.7 mmol) with 1-isopropyl-4,5-dihydro-1H-imidazol-2-amine hydrobromide (10.33 g, 49.7 mmol) as described for intermediate 1 gave 6.79 g (38% yield) of the title ester as white crystals; mp 131-132° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.22 (6H, d, J=6.8 Hz, 2×CH3), 1.31 (3H, t, J=7.1 Hz, CH3), 3.66 (2H, t, J=9 Hz, CH2), 4.13 (2H, t, J=9 Hz, CH2), 4.31 (2H, q, J=7.1 Hz, OCH2), 4.40 (1H, m, CH), 5.08 (2H, s, OCH2), 7.3-7.39 (3H, m, aromatics), 7.49 (2H, m, aromatics). Anal. Calcd for C19H23N3O4: C, 63.85; H, 6.48, N 11.75. Found: C, 63.57; H, 6.76; N, 11.98.

Provenance & Evidence