Oxalic Acid → (E)-3,4-Dimethoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

HRID 50893

반응식

HRID 50893 반응식
[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].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH:20]=[CH:21][C:22](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:53]([OH:58])(=[O:57])[C:54]([OH:56])=[O:55]>C(OCC)(=O)C>[C:53]([OH:58])(=[O:57])[C:54]([OH:56])=[O:55].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])/[CH:20]=[CH:21]/[C:22]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

참가 물질

6

반응물 4

HCID 971Oxalic AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 533992063,4-Dimethoxycinnamoylchloride

생성물 1

HCID 69914538(E)-3,4-Dimethoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 3,4-dimethoxycinnamoyl chloride (Ramamurthy, B.; Sugumaran, M. Synthesis, 1987, 523) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound. MW: 447.45; mp: 178.0-179.0° C.; 1H-NMR (DMSO) δ: 8.79-8.76 (1H, m), 8.18 (1H, td, J=7.7, 1.8 Hz), 7.83 (1H, d, J=16.1 Hz), 7.72 (2H, d, J=6.8 Hz), 7.63 (1H, dd, J=7.5, 5.0 Hz), 7.44 (1H, d, J=7.3 Hz), 7.34-7.15 (4H, m), 7.04 (1H, d, J=16.1 Hz), 6.99 (1H, t, J=8.1 Hz), 3.78 (6H, s).

후처리

  1. concentrationConcentration and recrystallization from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-a9169b2444a44cb29a3c0aaced8b9cf3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713482B2

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