N1-(pyridin-2-yl)benzene-1,2-diamine → (E)-2-[2-(Cyclohexyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

HRID 50903Notes

Reaction equation

HRID 50903 reaction equation
N1C=CC=CC=1NC1C=CC=CC=1N.C1(/C=C/C(Cl)=O)CCCCC1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1/[CH:41]=[CH:42]/[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH:43]1(/[CH:42]=[CH:41]/[C:33]2[N:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[N:34]=2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

4

Reactant 3

HCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 12542153(E)-3-cyclohexylacryloyl chloride

Product 1

HCID 22736655(E)-2-[2-(Cyclohexyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

Procedure

The titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-Cyclohexylacryloyl chloride (Amino, Y.; Kawada, K.; Toi, K.; Kumashiro, I.; Fukushima, K. Chem. Pharm. Bull., 1988, 36, 4426) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 303.41; mp: 105.0-106.0° C.; 1H-NMR (CDCl3) δ: 8.78-8.73 (1H, m), 7.96 (1H, ddd, J=7.7, 7.7, 1.8 Hz), 7.81-7.76 (1H, m), 7.49-7.39 (3H, m), 7.33-7.18 (2H, m), 7.11 (1H, dd, J=15.8, 7.3 Hz), 6.42 (1H, dd, J=15.8, 1.5 Hz), 2.26-2.12 (1H, m), 1.98-1.60 (5H, m), 1.39-1.10 (5H, m).

Sources & evidence

ORD record
ord-260c7122a5ec464c8631c2cd5331789b
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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