Hydrochloric Acid → (E)-2-(3-Methylstyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 50889Notes

Reaction equation

HRID 50889 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].[CH3:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=1)/[CH:19]=[CH:20]/[C:21]([Cl:23])=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:23].[CH3:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=1)/[CH:19]=[CH:20]/[C:21]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 5706559(e)-3-m-Tolylacryloyl chlorideHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736645(E)-2-(3-Methylstyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-methylcinnamoyl 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). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from 2-propanol/isopropyl ether yielded the titled compound. MW: 347.85; mp: 213.0-235.0° C.; 1H-NMR (DMSO) δ: 8.87-8.82 (1H, m), 8.33-8.20 (2H, m), 7.89 (2H, d, J=8.1 Hz), 7.81-7.74 (1H, m), 7.63-7.45 (5H, m), 7.40-7.24 (2H, m), 7.19 (1H, d, J=16.5 Hz), 2.35 (3H, s).

Workup

  1. concentrationConcentration and recrystallization from 2-propanol/isopropyl ether

Sources & evidence

ORD record
ord-d534f7bd466e45e598cd59e761454931
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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