N1-(pyridin-2-yl)benzene-1,2-diamine → HCID 22736724, compound

HRID 50897Notes

Reaction equation

HRID 50897 reaction equation
N1C=CC=CC=1NC1C=CC=CC=1N.[CH3:15][O:16]C1C=C(C=CC=1)/C=C/C(Cl)=O.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[C:35]1/[CH:43]=[CH:44]/[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[C:35]1/[CH:43]=[CH:44]/[C:45]1[CH:46]=[CH:47][C:48]([O:16][CH3:15])=[CH:49][CH:50]=1

Participants

4

Reactant 3

HCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 11367603(E)-3-methoxycinnamoyl chloride

Product 1

HCID 22736724HCID 22736724, compound

Procedure

The titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-methoxycinnamoyl chloride (Wiesler, W. T.; Nakanishi, K. J. Am. Chem. Soc., 1990, 112, 5574) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 327.39; mp: 145.5-146.5° C.; 1H-NMR (CDCl3) δ: 8.81-8.76 (1H, m), 8.04-7.96 (1H, m), 7.98 (1H, d, J=16.1 Hz), 7.85-7.79 (1H, m), 7.56-7.41 (5H, m), 7.37-7.22 (3H, m), 7.00 (1H, d, J=16.1 Hz), 6.88 (1H, d, J=8.4 Hz), 3.83 (3H, s).

Sources & evidence

ORD record
ord-7fbb027c788a4b32ae891c0077233e05
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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