Acetaldehyde → 5-(Benzoxazol-2-yl)-1-benzyl-2-methylbenzimidazole

HRID 74181Notes

Reaction equation

HRID 74181 reaction equation
[CH2:1]([NH:8][C:9]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:12][C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25](=O)[CH3:26].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:13]1[CH:14]=[CH:15][C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:25]([CH3:26])=[N:11][C:10]=2[CH:12]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988042-(2-Benzylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674982395-(Benzoxazol-2-yl)-1-benzyl-2-methylbenzimidazoleYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-benzylaminoanilin-5-yl)benzoxazole (see Working Example 17-2) (80.0 mg, 0.254 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 47.7 μL, 0.761 mmol) and oxone (102 mg, 0.165 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, and this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give an oil that was purified by silica gel column chromatography to yield the title compound (35.2 mg, 41% yield) as light brown crystals.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. customThe organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0f77a931e91d4ebeaa08f908fc57f930
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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