Acetaldehyde → 5-(Benzoxazol-2-yl)-2-methyl-1-n-propylbenzimidazole

HRID 74221Notes

Reaction equation

HRID 74221 reaction equation
[CH2:1]([NH:4][C:5]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:6]=1[NH2:7])[CH2:2][CH3:3].[CH:21](=O)[CH3:22].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:5]2[N:4]([CH2:1][CH2:2][CH3:3])[C:21]([CH3:22])=[N:7][C:6]=2[CH:8]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674986522-(2-n-Propylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674978095-(Benzoxazol-2-yl)-2-methyl-1-n-propylbenzimidazoleYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-n-propylaminoanilin-5-yl)benzoxazole (see Working Example 50-1) (148 mg, 0.554 mmol) in dimethylformamide (3 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 104 μL, 1.66 mmol) and oxone (341 mg, 0.554 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (46.6 mg, 29% yield) as gray crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6a50215966494c90a8979e66051f0044
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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