Hydrochloric Acid → (E)-5-Fluoro-(4-methoxystyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 382576Notes

Reaction equation

HRID 382576 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([NH2:15])[CH:3]=1.[CH3:16][O:17][C:18]1[CH:28]=[CH:27][C:21](/[CH:22]=[CH:23]/[C:24]([Cl:26])=O)=[CH:20][CH:19]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:26].[F:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:24](/[CH:23]=[CH:22]/[C:21]3[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:28][CH:27]=3)=[N:15][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 10976422trans-4-Methoxycinnamoyl chlorideHCID 227367454-fluoro-2-amino-N-(2-pyridyl)aniline

Product 1

HCID 22736773(E)-5-Fluoro-(4-methoxystyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Free base of the titled compound was prepared from 4-fluoro-2-amino-N-(2-pyridyl)aniline and (E)-4-methoxycinnamoyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate/ethanol to give the titled compound.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was recrystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-0fee7e0766ed4dd59074511224a76655
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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