(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole → (E)-5-Methoxy-2-[2-(2-methyl-3-furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole

HRID 50948Notes

Reaction equation

HRID 50948 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[CH3:17][C:18]1[O:19][CH:20]=[CH:21][C:22]=1/[CH:23]=[CH:24]/[C:25](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:3]2[N:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=3)[C:25](/[CH:24]=[CH:23]/[C:22]3[CH:21]=[CH:20][O:19][C:18]=3[CH3:17])=[N:1][C:2]=2[CH:14]=1

Participants

4

Reactant 3

HCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 227366532-amino-4-methoxy-N-(2-pyridyl)anilineHCID 22736728HCID 22736728, compound

Product 1

HCID 22736727(E)-5-Methoxy-2-[2-(2-methyl-3-furyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazoleYield 16%

Procedure

(E)-3-(2-Methyl-3-furyl)acrylic acid (0.30 g, 2 mmol) was dissolved into thionyl chloride (5 ml) and the mixture was heated to reflux for 80 min. Volatiles were removed by evaporation to give crude (E)-3-(2-methyl-3-furyl)acryloyl chloride. The titled compound was prepared from 2-amino4-methoxy-N-(2-pyridyl)aniline (0.43 g, 2 mmol) and (E)-3-(2-methyl-3-furyl)acryloyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). Recrystallization from a mixture of isopropyl ether (3 ml) and ethyl acetate (3 ml) to give 0.10 g (16%) of the titled compound. MW: 331.38; mp: 139.0-140.0° C.; 1H-NMR (CDCl3) δ: 8.75 (1H, dd, J=5.8, 2.2 Hz), 7.97 (1H, ddd, J=7.7, 7.7, 2.2 Hz), 7.79 (1H, d, J=15.8 Hz), 7.77-7.40 (2H, m), 7.33 (1H, d, J=8.8 Hz), 7.30 (1H, d, J=1.8 Hz), 7.24 (1H, d, J=2.0 Hz), 6.88 (1H, dd, J=9.2, 2.0 Hz), 6.72 (1H, d, J=15.8 Hz), 6.44 (1H, d, J=1.8 Hz), 3.89 (3H, s). 2.43 (3H, s).

Workup

  1. customobtained as
  2. customRecrystallization
  3. additionfrom a mixture of isopropyl ether (3 ml) and ethyl acetate (3 ml)

Sources & evidence

ORD record
ord-7f240cb0d71242bcb00ca15fb0cebfbf
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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