Acetic Anhydride → (E)-5-Acetylamino-1-(2-pyridyl)-2-styryl-1H-benzimidazole

HRID 382561Notes

Reaction equation

HRID 382561 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7](/[CH:9]=[CH:10]/[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.C(=O)(O)[O-].[Na+].[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([NH:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7](/[CH:9]=[CH:10]/[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22736667(E)-5-Amino-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736648(E)-5-Acetylamino-1-(2-pyridyl)-2-styryl-1H-benzimidazoleYield 61%

Procedure

(E)-5-Amino-1-(2-pyridyl)-2-styryl-1H-benzimidazole (199 mg, 0.64 mmol) was dissolved in acetic anhydride (2 ml) and the solution was allowed to maintain at room temperature for 30 mm. Then the reaction mixture was poured into saturated aqueous sodium bicarbonate solution (50 ml) and the aqueous mixture was extracted with ethyl acetate (100 ml). The organic extract was washed consecutively with water (50 ml) and brine (50 ml), dried (sodium sulfate) and concentrated in vacuo. The residual solids were purified by column chromatography (silica gel, 50 g; n-hexane/ethyl acetate (1/2)) and then recrystallized from ethyl acetate to afford 139 mg (61%) of the titled compound as yellow solids.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (100 ml)
  2. extractionThe organic extract
  3. washwas washed consecutively with water (50 ml) and brine (50 ml)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residual solids were purified by column chromatography (silica gel, 50 g; n-hexane/ethyl acetate (1/2))
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c44d60bd0d9140cbb0964e754ba5b8c0
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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