3-Furaldehyde → 5-(Benzoxazol-2-yl)-2-(furan-3-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74236

Reaction equation

HRID 74236 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[O:24]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25]1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:29]([C:26]3[CH:27]=[CH:28][O:24][CH:25]=3)=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 103513-FuraldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 498214595-(Benzoxazol-2-yl)-2-(furan-3-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in dimethylformamide (2 mL) was added 3-furaldehyde (80.7 mg, 0.840 mmol) and oxone (258 mg, 0.420 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 (171 mg, 69% yield) as pale yellow 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-3654201990e44b268913e761ca02e6fd
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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