Hydrogen Bromide → HCID 22736710, compound

HRID 382534Notes

Reaction equation

HRID 382534 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)/[CH:6]=[CH:7]/[C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:11]2[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=2[N:9]=1.Br.[OH-].[Na+].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>C(OCC)(=O)C.C(O)(=O)C>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[OH:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)/[CH:6]=[CH:7]/[C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:11]2[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=2[N:9]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 22736709HCID 22736709, compound

Product 1

HCID 22736710HCID 22736710, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to the literature procedure (Kawasaki, I.; Matsuda, K.; Kaneko, T. Bull. Chem. Soc. Jpn. 1971, 44, 1986.), a solution of (E)-2-(3-methoxystyryl)-1-(2-pyridyl)-1H-benzimidazole (76 mg, 0.23 mmol), glacial acetic acid (10 ml) and 48% aqueous solution of hydrogen bromide (5 ml) was heated under reflux condition for 4 h. The resulting solution was neutralized by sodium hydroxide pellet and this mixture was extracted with dichloromethane (3×15 ml). Combined organic layer was dried (magnesium sulfate) and filtered. The filtrate was concentrated then the residue (39 mg, 54%) and oxalic acid (12 mg, 0.12 mmol) were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound.

Workup

  1. temperatureunder reflux condition for 4 h
  2. extractionthis mixture was extracted with dichloromethane (3×15 ml)
  3. dry with materialCombined organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. concentrationConcentration and recrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-a2191dfdcdf34d2dbd63a2e0bd4bb510
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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