Hydrochloric Acid → (E)-1-(2-Pyridyl)-2-(4-fluorostyryl)-1H-benzimidazole hydrochloride

HRID 50896

Reaction equation

HRID 50896 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].[F:15][C:16]1[CH:26]=[CH:25][C:19](/[CH:20]=[CH:21]/[C:22]([Cl:24])=O)=[CH:18][CH:17]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:24].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=[C:22]1/[CH:21]=[CH:20]/[C:19]1[CH:25]=[CH:26][C:16]([F:15])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 5706471(E)-4-Fluorocinnamoyl chlorideHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736636(E)-1-(2-Pyridyl)-2-(4-fluorostyryl)-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)-4-fluorocinnamoyl 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 ethyl acetate/ethanol yielded the titled compound. MW: 351.81; mp:>230° C.; 1H-NMR (CDCl3) δ: 9.10 (1H, d, J=16.5 Hz), 8.89-8.84 (1H, m), 8.24-8.12 (2H, m), 7.72-7.43 (6H, m), 7.07 (2H, dd, J=8.4, 8.4 Hz), 6.91 (1H, d, J=16.5 Hz), 6.82 (1H, dd, J=8.8, 8.8 Hz).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-00dfd05e278e466886f6af3e71f19dd9
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

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