Water → HCID 178423499, compound

HRID 1696616Notes

Reaction equation

HRID 1696616 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[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.O>C1COCC1>[CH3:11][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

6

Reactant 4

HCID 962WaterHCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178423448HCID 178423448, compound

Product 1

HCID 178423499HCID 178423499, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

to a solution of 0.82 g of 2-mercapto-5-methyl benzimidazole (5 mmoles) in 10 ml of dry THF is added 200 mg of sodium hydride suspension (60% suspension in mineral oil) (5 mmoles). The reaction mixture is heated at reflux temperature for ½ hour. The mixture is then cooled to room temperature and 0.71 g of 5-nitrofuraldehyde (5 mmoles) in 5 ml of THF is added dropwise. The reaction mixture is stirred for ½ hour and then poured into 200 ml of water. The mixture is extracted twice with 75 ml of EtOAc. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated. The crude product is purified on silica gel using DCM/MeOH 97/3 as eluent. 1.07 g of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is isolated as a black glassy solid (yield=83%). Analytical LC/MS method A: ([M+H]+): 259, RT: 3.64 min (gradient 0 to 50% acetonitrile in 7 min).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for ½ hour
  3. extractionThe mixture is extracted twice with 75 ml of EtOAc
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product is purified on silica gel

Sources & evidence

ORD record
ord-0ea0f1fa1aab47feb05c371cc59b639b
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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