Hydrochloric Acid → (E)-1-(6-Chloro4-pyrimidyl)-2-styryl-1H-benzimidazole hydrochloride

HRID 50880Notes

Reaction equation

HRID 50880 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:18][C:19]1[CH:24]=[C:23]([Cl:25])[N:22]=[CH:21][N:20]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:18].[Cl:25][C:23]1[N:22]=[CH:21][N:20]=[C:19]([N:10]2[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=[C:9]2/[CH:1]=[CH:2]/[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 709434,6-DichloropyrimidineHCID 2429652-(2-Phenylethenyl)-1h-benzimidazoleHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736683(E)-1-(6-Chloro4-pyrimidyl)-2-styryl-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from 2-styryl-1H-benzimidazole and 4,6-dichloropyrimidine according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method B). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate-hexane to give the titled compound. MW: 376.33; mp: 203.0-204.0° C.; 1H-NMR (DMSO) δ: 9.27 (1H, d, J=1.1 Hz), 8.15 (1H, d, J=1.1 Hz), 8.02-7.94 (1H, m), 7.80-7.72 (4H, m), 7.49-7.27 (6H, m).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f636f20b75234af6a44a1aed3f7a9706
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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