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

HRID 50891Notes

Reaction equation

HRID 50891 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].[Cl:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=1)/[CH:19]=[CH:20]/[C:21](Cl)=O.Cl>CO>[ClH:15].[Cl: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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 11008963(2E)-3-(3-chlorophenyl)prop-2-enoyl chloride

Product 1

HCID 22736634(E)-2-(3-Chlorostyryl)-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-Chlorocinnamoyl 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-H-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/ethanol yielded the titled compound. MW: 368.27; mp:>230° C.; 1H-NMR (DMSO) δ: 8.85-8.81 (1H, m), 8.31-8.22 (1H, m), 8.20 (1H, d, J=16.1 Hz), 7.90-7.81 (3H, m), 7.78-7.72 (1H, m), 7.68-7.43 (6H, m), 7.33 (1H, d, J=16.1 Hz).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-4829af47f9494bf3a551ebfb549ce0d8
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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