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

HRID 1463329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463329
[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

Komponenten

8

Edukt 3

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

Produkt 1

HCID 69013000HCID 69013000, VerbindungAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a3312b529b3c48a9b659def156b2073d
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300506

Notizen zur Reaktion

Wird geladen…