Cinnamoyl Chloride → (E)-6-Methyl-1-(2-pyridyl)-2-styryl-1H-benzimidazole

HRID 50936

Reaction equation

HRID 50936 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[C:16](Cl)(=O)/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[CH3:15][C:12]1[CH:13]=[CH:14][C:2]2[N:1]=[C:16](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=3)[C:3]=2[CH:11]=1

Participants

4

Reactant 3

HCID 5354261Cinnamoyl ChlorideHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 227367082-amino-5-methyl-N-(2-pyridyl)aniline

Product 1

HCID 22736763(E)-6-Methyl-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Procedure

The titled compound was prepared from 2-amino-5-methyl-N-(2-pyridyl)aniline and (E)-cinnamoyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 311.39; mp: 164.0-164.9° C.; 1H-NMR (CDCl3) δ: 8.80-8.76 (1H, m), 8.03-7.92 (2H, m), 7.71 (1H, d, J=8.1 Hz), 7.54-7.42 (4H, m), 7.38-7.23 (4H, m), 7.19-7.14 (1H, m), 7.11 (1H, d, J=16.1 Hz), 2.46 (3H, s).

Sources & evidence

ORD record
ord-dedc25f6e8104377816b60455501a15a
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

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