Acetaldehyde → 5-(Benzoxazol-2-yl)-1-(3-methoxyphenyl)-2-methylbenzimidazole

HRID 74201Notes

Reaction equation

HRID 74201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:13][C:11]=2[NH2:12])[CH:6]=[CH:7][CH:8]=1.[CH:26](=O)[CH3:27].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:14]1[CH:15]=[CH:16][C:10]2[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:26]([CH3:27])=[N:12][C:11]=2[CH:13]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674994272-(2-(3-Methoxyphenyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674982285-(Benzoxazol-2-yl)-1-(3-methoxyphenyl)-2-methylbenzimidazoleYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-(3-methoxyphenyl)aminoanilin-5-yl)benzoxazole (see Working Example 31-1) (55.0 mg, 0.166 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 31.2 μL, 0.405 mmol) and oxone (66.3 mg, 0.108 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 (17.3 mg, 29% 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-a146b8ddecdc424cbfd0bb94d34d4a81
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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