3,4-dihydro-2H-pyran → HCID 69013000, compound

HRID 1647780Notes

Reaction equation

HRID 1647780 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:5][CH:4]=1)[NH2:2].C([O-])(=O)C.[Na+].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>O.C(O)C.C(OCC)(=O)C.C(Cl)Cl>[OH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=[N:2][NH:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:11])=[O:12])=[CH:7][CH:8]=1

Participants

8

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 517045Sodium AcetateHCID 132861074-hydrazinyl-N,N-dimethyl-benzenemethanesulfonamide

Product 1

HCID 69013000HCID 69013000, compoundYield 28.2%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.02 g (18.9 mmol, 1.0 equiv.) of 4-hydrazinyl-N,N-dimethyl-benzenemethanesulfonamide in 20 mL of water and 20 mL of ethanol was added sufficient sodium acetate to raise the pH to four. To the resulting slurry was added 1.90 mL (20.8 mmol, 1.1 equiv.) of 3,4-dihydro-2H-pyran. The reaction was stirred for sixteen hours then diluted with 200 mL of ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate, dried over anhydrous sodium sulfate and concentrated in vacuo to yield an oil. Chromatography on silica gel using 5% methanol in methylene chloride containing 0.5% concentrated aqueous ammonium hydroxide yielded 1.67 g (28%) of pure 4-[2-(5-hydroxypentylidene)hydrazinyl]-N,N-dimethylbenzenemethanesulfonamide as an oil.

Workup

  1. temperatureto raise the pH to four
  2. washThe organic layer was washed with 10% aqueous potassium carbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield an oil

Sources & evidence

ORD record
ord-2c56792a5d024b00a0adec5c7d89ecb7
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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