N1-(pyridin-2-yl)benzene-1,2-diamine → (E)-1-(2-Pyridyl)-2-[2-(2-thienyl)ethenyl]-1H-benzimidazole
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].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1/[CH:20]=[CH:21]/[C:22](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1>>[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:16]1[S:15][CH:19]=[CH:18][CH:17]=1Participants
4
Procedure
The tilled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-(2-thienyl)acryloyl chloride (Aitken, R. A.; Boeters, C.; Morrison, J. J. J. Chem. Soc. Perkin. Trans. 1, 1994, 17, 2473) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 303.39; mp: 130.0-131.0° C.; 1H-NMR (CDCl3) δ: 8.77 (1H, ddd, J=4.8, 1.8, 0.7 Hz), 8.12 (1H, d, J=15.8 Hz), 8.02 (1H, ddd, J=8.1,8.1, 1.8 Hz), 7.84-7.79 (1H, m), 7.51 (1H, ddd, J=8.1, 1.1, 0.7 Hz), 7.49-7.43 (2H, m), 7.37-7.18 (3H, m), 7.20 (1H, dd, J=3.7,0.7 Hz), 7.02 (1H, dd, J=4.8, 3.7 Hz), 6.94 (1H, d, J=15.8 Hz).
Sources & evidence
- ORD record
- ord-36d30027d4d04e029bff37f9b0e8492e
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713482B2
Reaction notes
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