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

HRID 74223Notes

Reaction equation

HRID 74223 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:7]=1[NH2:8].[CH:22](=O)[CH3:23].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:6]2[N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:22]([CH3:23])=[N:8][C:7]=2[CH:9]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674991982-(2-(2-Methoxyethyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674989585-(Benzoxazol-2-yl)-1-(2-methoxyethyl)-2-methylbenzimidazoleYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-(2-methoxyethyl)aminoanilin-5-yl)benzoxazole (see Working Example 51-1) (98 mg, 0.346 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 65.1 μL, 1.66 mmol) and oxone (213 mg, 0.346 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 (41.4 mg, 39% yield) as light brown 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-6b56125deb1f497cbc5186cff542b680
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

Loading…