N1-(pyridin-2-yl)benzene-1,2-diamine → (E)-2-[2-(3-Furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

HRID 50907Notes

Reaction equation

HRID 50907 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[O:15]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22](Cl)=O)=[CH:16]1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[O:15]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=2)=[CH:16]1

Participants

4

Reactant 3

HCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 22736687(E)-3-(Furan-3-yl)acryloyl chloride

Product 1

HCID 9838855(E)-2-[2-(3-Furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

Procedure

The titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-(3-furyl)acryloyl chloride (Shizuri, Y.; Ojika, M.; Yamada, K. Tetrahedron Lett., 1981, 22, 4291) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 287.32; mp: 162.5-164.0° C.; 1H-NMR (CDCl3) δ: 8.79-8.75 (1H, m), 7.99 (1H ddd, J=7.7, 7.7, 1.8 Hz), 7.87 (1H, d, J=15.8 Hz), 7.83-7.78 (1H, m), 7.64-7.62 (1H, m), 7.53-7.39 (4H, m), 7.37-7.22 (2H, m), 6.85 (1H, d, J=15.8 Hz), 6.55 (1H, d, J=1.8 Hz).

Sources & evidence

ORD record
ord-4cb2fd087c9b41958f4234a629f48467
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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