Hydrochloric Acid → (E)-2-[2-(Cyclohexyl)ethenyl]-5-methoxy-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 50945Notes

Reaction equation

HRID 50945 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:5]([NH2:16])[CH:4]=1.[CH:17]1(/[CH:23]=[CH:24]/[C:25]([Cl:27])=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:27].[CH:17]1(/[CH:23]=[CH:24]/[C:25]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:6]3[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:16]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 12542153(E)-3-cyclohexylacryloyl chlorideHCID 227366532-amino-4-methoxy-N-(2-pyridyl)aniline

Product 1

HCID 22736712(E)-2-[2-(Cyclohexyl)ethenyl]-5-methoxy-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from 4-methoxy-2-amino-N-(2-pyridyl)aniline and (E)-3-Cyclohexylacryloyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate-hexane yielded the titled compound. MW: 369.90; mp: 168.0-169.0° C.; 1H-NMR (DMSO) δ: 8.80-8.76 (1H, m), 8.24 (1H, td, J=7.7, 1.8 Hz), 7.82-7.71 (2H, m), 7.46 (1H, d, J=9.2 Hz), 7.34-7.25 (2H, m), 7.09 (1H, dd, J=9.2, 2.6 Hz), 6.42 (1H, dd, J=15.8, 1.1 Hz), 3.56 (3H, s), 2.40-2.20 (1H, m), 1.80-1.55 (5H, m), 1.40-1.05 (5H, m).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3a4134a7f0c143a18fd9535506596a46
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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