Water → HCID 23116374, compound

HRID 495207Notes

Reaction equation

HRID 495207 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Cs+].[Cs+].[C:7]1(S)[CH:12]=[CH:11][CH:10]=[CH:9]C=1.[OH2:14].[C:15](#[N:17])[CH3:16]>>[O:2]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:1]1[O:4][CH2:16][CH2:15][NH:17][CH2:7][C:12]1[O:14][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 7969ThiophenolHCID 10796Cesium carbonate

Product 1

HCID 23116374HCID 23116374, compoundYield 65%

Procedure

N-Furfuryl-2-nitro-N-[2-(tetrahydropyran-2-yloxy)ethyl]benzenesulfonamide (10 g, 24 mmol) obtained in Reference Example 11, Step 3 was dissolved in acetonitrile (0.10 L). To the solution were added cesium carbonate (24 g, 74 mmol) and thiophenol (3.0 mL, 29 mmol), followed by stirring for 2 hours, while the temperature was raised from room temperature to 80° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-methanol/ethyl acetate=15/85) to obtain N-[2-(tetrahydropyran-2-yloxy)ethyl]furfurylamine (3.6 g, 65%).

Workup

  1. temperaturewas raised from room temperature to 80° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-methanol/ethyl acetate=15/85)

Sources & evidence

ORD record
ord-2cbea2878fb14e3cbf5fbc66c7ba3492
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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