Hydrochloric Acid → 6-(Benzenesulfonyl)-2,3-dihydropyridazin-3-one

HRID 1742278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742278
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[OH2:9].O.[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].[OH-].[Na+].Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCOCC1>[C:11]1([S:17]([C:2]2[CH:7]=[CH:6][C:5](=[O:9])[NH:4][N:3]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673313,6-DichloropyridazineHCID 23681562Benzenesulfinic acid, sodium salt, dihydrate

Produkt 1

HCID 117014376-(Benzenesulfonyl)-2,3-dihydropyridazin-3-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3,6-dichloropyridazine (50 g), sodium benzenesulfinate dihydrate (100 g), benzyltrimethylammonium chloride (62.3 g), and 1,4-dioxane (335 ml) was stirred for 3 hours at 100° C. After being cooled to room temperature, aqueous solution of sodium hydroxide (510 ml) was added to the mixture, and the mixture was stirred for 0.5 hour at 100° C. The reaction mixture was cooled in a water bath and acidified with 36% hydrochloric acid (35 ml). The precipitate formed was collected, washed well with water, and dried to give 6-phenylsulfonyl-3-oxo-2,3-dihydropyridazine (54.7 g).

Aufarbeitung

  1. temperatureAfter being cooled to room temperature
  2. stirringthe mixture was stirred for 0.5 hour at 100° C
  3. temperatureThe reaction mixture was cooled in a water bath
  4. customThe precipitate formed
  5. customwas collected
  6. washwashed well with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bd7e5a0f947a452c980a4552d273cfdd
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05338743

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