5-Nitrofurfural → HCID 86623873, compound

HRID 1696631Notes

Reaction equation

HRID 1696631 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[SH:10].[H-].[Na+].[N+]([C:16]1[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=1)([O-])=O>O1CCCC1>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[S:10][C:16]1[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178527819HCID 178527819, compound

Product 1

HCID 86623873HCID 86623873, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1H-Imidazo[4,5-b]pyridine-2-thiol (1.51 g, 10.0 mmol) is suspended into 80 mL of tetrahydrofuran under argon. Then, 0.72 g (15.0 mmol) of sodium hydride is added. The reaction mixture is stirred at room temperature until gas evolution has ceased. 5-Nitro-2-furaldehyde (1.41 g, 10.0 mmol) is then added and the reaction mixture is stirred at room temperature for 2.5 h, upon which it is poured on ice and extracted 3 times with ethyl acetate. The organic extracts are combined, washed with brine, dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate, filtered, washed with ethyl acetate and dried under reduced pressure. 1.34 g of 5-(1H-imidazo[4,5-b]pyridin-2-ylsulfanyl)-furan-2-carbaldehyde is obtained as a crystalline light-brown powder. mp: 188° C.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 2.5 h, upon which it
  2. additionis poured on ice
  3. extractionextracted 3 times with ethyl acetate
  4. washwashed with brine
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is recrystallized from ethyl acetate
  9. filtrationfiltered
  10. washwashed with ethyl acetate
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-abe3cc492d054670a6135988cd63a8b6
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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