Acetaldehyde → 5-(Benzoxazol-2-yl)-1-(4-fluorophenyl)-2-methylbenzimidazole

HRID 74204Notes

Reaction equation

HRID 74204 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:12][C:10]=2[NH2:11])=[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]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:25]([CH3:26])=[N:11][C:10]=2[CH:12]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674981322-(2-(4-Fluorophenyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674981745-(Benzoxazol-2-yl)-1-(4-fluorophenyl)-2-methylbenzimidazoleYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-(4-fluorophenyl)aminoanilin-5-yl)benzoxazole (see Working Example 34-1) (38.0 mg, 0.119 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 22.6 μL, 0.360 mmol) and oxone (73.2 mg, 0.119 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 (20.0 mg, 49% 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-ba05cdd7cd0a4be1a10844316c68f610
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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