5-Nitrofurfural → HCID 178519731, compound

HRID 1696676Notes

Reaction equation

HRID 1696676 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[N+]([C:17]1[O:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=1)([O-])=O>O1CCCC1>[F:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][C:17]3[O:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=3)=[N:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 34348856-fluoro-1H-benzimidazole-2-thiol

Product 1

HCID 178519731HCID 178519731, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-mercapto-5-fluoro-benzimidazole (2.24 g, 13.3 mmol) in tetrahydrofuran (10 ml) is added dropwise to a mixture of sodium hydride (60% dispersion in mineral oil, 0.852 g, 21.3 mmol) and tetrahydrofuran (5 ml). The mixture is stirred at room temperature for 2 hours. A solution of 5-nitro-2-furaldehyde (1.88 g, 13.3 mmol) in tetrahydrofuran (15 ml) is then added dropwise over a 15 minute period and the mixture is stirred for 2 hours at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is dissolved in 200 ml of ethyl acetate and washed with water (2×60 ml). The organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue is purified on a silica gel column (40 g) eluted with dichloromethane to yield 700 mg of 5-(5-fluoro-1H-benzoimidazol-2-ylsulfanyl)-furan-2-carbaldehyde as an orange powder. Yield=20%. Analytical LC/MS (method B): retention time=3.08 min., m/z=263.05 (positive ion mode).

Workup

  1. stirringthe mixture is stirred for 2 hours at room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in 200 ml of ethyl acetate
  4. washwashed with water (2×60 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified on a silica gel column (40 g)
  8. washeluted with dichloromethane

Sources & evidence

ORD record
ord-f08dbef380c94de4af123ef6c8b390ba
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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