Acetic Acid → HCID 10249791, compound

Participants

Reaction Conditions

Reaction Steps

To 100 mL acetic acid and 4 mL concentrated sulfuric acid, was added 1.80 g (4.22 mmol) of 11 and the mixture was heated at 100° C. for 5 hours. After evaporating the solvents down to ca 5 mL, the oily residue was poured over 100 mL of ice water, neutralized with sodium carbonate, and the resulting solution extracted with 3×100 mL portions of chloroform. The combined extracts were evaporated to a small volume, placed on a silica column, and purified by flash chromatography employing ethyl acetate as the eluant. The product fraction was collected and evaporated to dryness. Recrystallization was carried out by redissolving the product in a minimum amount of chloroform followed by addition of hexane: 1.10 g (67%) yield; mp 223°-224° C.; TLC (ethyl acetate/methanol [9:1], Rf =0.22; IR (KBr pellet) 1688, 1614, 1474, 1428, 1375, 1342, 1269, 1097, 1036, 797 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ4.58 (4H, s, methylenes), 3.93, 3.62 and 3.42 (18H, 3×s, N- and O-methyls, no assignments made); mass spectrum (EI mode) m/z 390 (P+). Anal. Calcd for C18H22N4O6. 0.3H2O: C, 54.75; H, 5.74; N, 14.19. Found: C, 54.39; H, 5.63; N, 14.25.

Provenance & Evidence