Phthalic Anhydride → HCID 19815432, compound

Participants

Reaction Steps

To an acetonitrile solution (12 mL) of 1-(4-aminobenzyl)-4-chloro-5-hydroxymethyl-2-(2-methoxyethyl)imidazole (150 mg, 0.51 mmol) was added an acetonitrile solution (2 mL) of phthalic anhydride (75 mg, 0.51 mmol). After stirring overnight at room temperature a light yellow precipitate was produced. The mixture was cooled to 0°, filtered with suction onto a fine fritted funnel and the solid was washed with cold acetonitrile, chloroform and finally ether (2 mL each) to afford 180 mg (80%) of light tan solid, m.p. 185°-186° (dec.). NMR (200 MHz, CDCl3 /CD3OD) δ8.05-6.95 (m, 8H); 5.30 (s, 2H); 4.50 (s, 2H); 3.60 (t, 2H, 5 Hz); 3.25 (s, 3H); 2.8 (t, 2H, 5 Hz). Mass Spec. Calcd. for C22H18ClN3O3 (M-2H2O): 407.1037. Found: 407.1031.

Provenance & Evidence