4-Hydroxybiphenyl → HCID 478195, 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([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)=NC(Cl)=O>>[CH3:25][CH:24]([C:11]1[N:12]=[C:13]([CH2:22][O:23][C:28]([NH:27][C:31]([O:33][C:43]2[CH:44]=[CH:45][C:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:41][CH:42]=2)=[O:32])=[O:30])[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]=1[S:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)[CH3:26]Participants
Procedure
The compound 89 (245 mg, 0.6 mmol) was converted to the iminodicarboxylate with N-4-biphenyloxycarbonyl isocyanate prepared from 4-phenylphenol (187 mg, 1.1 mmol) and N-chlorocarbonylisocyanate (106 mg, 1 mmol) in the same manner as the example 82 to give the compound 103 (215 mg, 55%). Mp 105-107° C. Rf 0.40 (EtOAc). 1H-NMR (CDCl3): δH1.32 (6 H, d, J 6.9 Hz, (CH3)2CH), 3.21 (1 H, sep, J 6.8 Hz, (CH3)2CH), 5.31 (2 H, s, NCH2), 5.33 (2 H, s, OCH2), 6.72 (2 H, d, J 1.5 Hz, arom 2- and 6-H), 6.78 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.06 (1 H, t, J 1.5 Hz, arom 4-H), 7.18 - 7.60 (9 H, m, 4-phenylphenyl), 7.82 (1 H, bs, NH), 8.46 (2 H, d-like, 4-pyridyl 3- and 5-H). IR(CHCl3)cm-1 : 3418 (NH), 1817 and 1747 (OOCNCOO). Elementary analysis (for C33H28N4O4SCl2) Calcd.: C, 61.21% H, 4.36% N, 8.65% S, 4.95% Cl, 10.95% Found: C, 61.06% H, 4.38% N, 8.64% S, 4.94% Cl, 10.78%
Sources & evidence
- ORD record
- ord-57ea9f3396e74a1e9e50d0b125ae9f21
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054591
Reaction notes
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