Acetic Anhydride → HCID 13371391, compound

Participants

Reaction Steps

N-Benzoylsarcosine (3.86 g, 0.020 mol) was dissolved in 7 mL (0.070 mol) of acetic anhydride and heated until a yellow color was observed. Forty milliliters of toluene was added to the reaction flask after the color change was observed. After stirring for 15 minutes, 3.16 g (0.020 mol) of 1,4-naphthoquinone was added. The resulting black mixture was heated for 1.5 hours, then stirred at room temperature overnight. The mixture was filtered to yield 1.13 g (19%) of yellow-brown solid. The solid was recrystallized several times from toluene to give bright yellow crystals: mp 268°-271° C.; IR 1655 and 1645 (C=0) cm-1 ; H-1 NMR (CDCl3) δ 3.60 (s, 3, NCH3), 7.10-7.75 (complex m and s, 8, ArH and pyrrole H), 7.95-8.30 (m, 2, ArH); MS m/e 287 M+.

Provenance & Evidence