Oxalic Acid → (E)-2-Styryl-1-(4-trifloromethyl-2-Pyrimidyl)-1H-benzimidazole oxalate

HRID 50878Notes

Reaction equation

HRID 50878 reaction equation
[CH:1]([C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:19]1[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][N:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:52]([OH:57])(=[O:56])[C:53]([OH:55])=[O:54]>C(OCC)(=O)C>[C:52]([OH:57])(=[O:56])[C:53]([OH:55])=[O:54].[CH:1](/[C:9]1[N:10]([C:19]2[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][N:20]=2)[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736656(E)-2-Styryl-1-(4-trifloromethyl-2-Pyrimidyl)-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 2-styryl-1H-benzimidazole and 2-Chloro-4-trifluromethyl-pyrimidine according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method B). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound. MW: 411.37; mp: 189.0-191.0° C.; 1H-NMR (DMSO) δ: 9.42 (1H, d, J=4.8 Hz), 8.20-8.13 (1H, m), 8.10 (1H, dd, J=4.8, 1.3 Hz), 8.01 (1H, d, J=16.1 Hz), 7.91 (1H, d, J=16.1 Hz), 7.79-7.71 (1H, m), 7.68 (1H, d, J=7.0 Hz), 7.47-7.34 (6H, m).

Workup

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

Sources & evidence

ORD record
ord-5f5ddb4db6db42cf938581cd509d5a5d
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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