N1-(pyridin-2-yl)benzene-1,2-diamine → HCID 22736654, compound

HRID 50899Notes

Reaction equation

HRID 50899 reaction equation
N1C=CC=CC=1NC1C=CC=CC=1N.CC1C=C(C=CC=1)/C=C/[C:21](Cl)=[S:22].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1/[CH:42]=[CH:43]/[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1/[CH:42]=[CH:43]/[C:44]1[CH:45]=[CH:46][C:47]([S:22][CH3:21])=[CH:48][CH:49]=1

Participants

4

Reactant 3

HCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 22736701(E)-3-methylthiocinnamoyl chloride

Product 1

HCID 22736654HCID 22736654, compound

Procedure

The titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-3-methylthiocinnamoyl chloride (Miller, R. D.; Reiser, O. J. Heterocycl. Chem. 1993, 30, 755) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). MW: 343.46; mp: 139.6-140.6° C.; 1H-NMR (CDCl3) δ: 8.78 (1H, dd, J=5.1, 2.2 Hz), 8.00 (1H, ddd, J=7.7, 7.7, 2.2 Hz), 7.96 (1H, d, J=16.1 Hz), 7.83 (1H, d, J=7.3 Hz), 7.54-7.39 (5H, m), 7.38-7.18 (4H, m), 7.10 (1H, d, J=16.1 Hz), 2.49 (3H, s).

Sources & evidence

ORD record
ord-590471c696274991b592646b1b528ce3
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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