Water → HCID 178455022, compound

HRID 1696619Notes

Reaction equation

HRID 1696619 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[N+]([C:24]1[O:28][C:27]([CH:29]=[O:30])=[CH:26][CH:25]=1)([O-])=O.O>O1CCCC1>[C:15]([Si:12]([CH3:13])([CH3:14])[O:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][C:24]3[O:28][C:27]([CH:29]=[O:30])=[CH:26][CH:25]=3)=[N:3][C:4]=2[CH:10]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178455021HCID 178455021, compound

Product 1

HCID 178455022HCID 178455022, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Aldehyde intermediate preparation: A solution of 2-mercapto-5-(tert-butyl-dimethyl-silanyloxy)-benzimidazole (2.07 g, 7.38 mmol) in tetrahydrofuran (15 ml) is added dropwise to a mixture of sodium hydride (60% dispersion in mineral oil, 0.472 g, 11.8 mmol) and tetrahydrofuran (5 ml) at 0° C. The mixture is stirred at room temperature for 3 hours. A solution of 5-nitro-2-furaldehyde (1.04 g, 7.38 mmol) in tetrahydrofuran (10 ml) is then added dropwise over a 15 minute period and the mixture is stirred for 16 hours at room temperature. Water (10 ml) is then added and the reaction mixture is concentrated under reduced pressure. The residue is dissolved in a minimal volume of ethyl acetate and is filtered through a silica gel plug (20 ml) that is eluted with 500 ml of ethyl acetate. The organic filtrates are concentrated under reduced pressure and are purified on a silicagel column (120 g) eluted with a mixture of cyclohexane and ethyl acetate (7/3, v/v) to yield 1.4 g of 5-[5-(tert-butyl-dimethyl-silanyloxy)-1H-benzimidazol-2-ylsulfanyl]-furan-2-carbaldehyde as a brown oil. Yield=51%. Analytical LC/MS (method B): retention time=4.62 min., m/z=375.05 (positive ion mode).

Workup

  1. stirringthe mixture is stirred for 16 hours at room temperature
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in a minimal volume of ethyl acetate
  4. filtrationis filtered through a silica gel plug (20 ml) that
  5. washis eluted with 500 ml of ethyl acetate
  6. concentrationThe organic filtrates are concentrated under reduced pressure
  7. customare purified on a silicagel column (120 g)
  8. washeluted with a mixture of cyclohexane and ethyl acetate (7/3

Sources & evidence

ORD record
ord-ab344a3f4eff40a78a80a484004731fc
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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