5-Nitrofurfural → 5-(6-trifluoromethyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde

HRID 1696658Notes

Reaction equation

HRID 1696658 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].[N+]([C:20]1[O:24][C:23]([CH:25]=[O:26])=[CH:22][CH:21]=1)([O-])=O>O1CCCC1>[F:12][C:11]([F:14])([F:13])[C:8]1[CH:9]=[CH:10][C:4]2[N:3]=[C:2]([S:1][C:20]3[O:24][C:23]([CH:25]=[O:26])=[CH:22][CH:21]=3)[NH:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydride2×HCID 178506086HCID 178506086, compound

Product 1

HCID 866238825-(6-trifluoromethyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehydeYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Aldehyde intermediate preparation: 2-mercapto-6-trifluoromethyl-1H-benzimidazole (0.65 g, 2.98 mmol) dissolved in 5 ml of anhydrous tetrahydrofuran is added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 0.095 g, 3.16 mmol) in anhydrous tetrahydrofuran (2 ml) over a 20 minutes period. The reaction mixture is stirred for 2 hours at room temperature. Then 5-nitro-2-furaldehyde (0.42 g, 2.98 mmol) dissolved in 5 ml of anhydrous tetrahydrofuran is added dropwise over a 15 minutes period and the reaction mixture is stirred at room temperature for an additional 16 hours period. Sodium hydride (67 mg, 2.23 mmol) is then added and the reaction mixture is stirred for an additional 2 hours period at room temperature. The reaction mixture is then concentrated under reduced pressure, dissolved in ethyl acetate (50 ml) and washed with water (2×10 ml). The organic phase is dried over MgSO4, concentrated under reduced pressure and the residue is triturated in diisopropylether, collected by filtration and dried under vacuum to yield 720 mg of 5-(6-trifluoromethyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde as a beige powder. Yield=77%, Analytical LC/MS (method B): retention time=3.73 min., m/z=313.01 (positive ion mode).

Workup

  1. additionis added dropwise over a 15 minutes period
  2. stirringthe reaction mixture is stirred at room temperature for an additional 16 hours period
  3. stirringthe reaction mixture is stirred for an additional 2 hours period at room temperature
  4. concentrationThe reaction mixture is then concentrated under reduced pressure
  5. dissolutiondissolved in ethyl acetate (50 ml)
  6. washwashed with water (2×10 ml)
  7. dry with materialThe organic phase is dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customthe residue is triturated in diisopropylether
  10. filtrationcollected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-ecee202055884ab1be15e69073a1ddbf
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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