1-Naphthol → HCID 478196, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][OH:23])=[N:12][C:11]=2[CH:24]([CH3:26])[CH3:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:27]([C:31]([O-:33])=[O:32])[C:28]([O-:30])=O.[C:34]1(O)[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1.C(=O)=NC(Cl)=O>>[NH:27]([C:28]([O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:24]([CH3:26])[CH3:25])[N:12]=1)=[O:30])[C:31]([O:33][C:42]1[C:43]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:39]=[CH:40][CH:41]=1)=[O:32]Participants
Procedure
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%
Sources & evidence
- ORD record
- ord-7ec5ff48c2264c069cbfef8c0515705f
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054591
Reaction notes
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