1-Naphthol → HCID 478196, compound

Participants

Reaction Steps

The compound 89 (245 mg, 0.6 mmol) was converted to the iminodicarboxylate with N-1-naphthyloxycarbonyl isocyanate prepared from 1-naphthol (158 mg, 1.1 mmol) and N-chlorocarbonylisocyanate (106 mg, 1 mmol) in the same manner as the example 82 to give the compound 104 (169 mg, 45%). Mp 166-167° C. Rf 0.38 (EtOAc). 1H-NMR (CDCl3): δH1.33 (6 H, d, J 6.8 Hz, (CH3)2CH), 3.21 (1 H, sep, J 6.9 Hz, (CH3)2CH), 5.33 (4 H, s, NCH2 and OCH2), 6.72 (2 H, d, J 1.6 Hz, arom 2- and 6-H), 6.78 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.05 (1 H, t, J 1.6 Hz, arom 4-H), 7.30 - 7.91 (7 H, m, 1-naphthyl), 8.04 (1 H, bs, NH), 8.45 (2 H, d-like, 4-pyridyl 3- and 5-H). IR(CHCl3)cm-1 : 3418 (NH), 1820 and 1748 (OOCNCOO). Elementary analysis (for C31H26N4O4SCl2) Calcd.: C, 59.91% H, 4.22% N, 9.01% S, 5.16% Cl, 11.41% Found: C, 59.34% H, 4.12% N, 9.27% S, 5.24% Cl, 11.16%

Provenance & Evidence