Sodium methanethiolate → 4,5-Dimethyl-6-(methylthio)pyridazin-3-amine

HRID 1501346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1501346
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[CH3:11][S-:12].[Na+]>C(O)C>[CH3:9][C:4]1[C:3]([CH3:10])=[C:2]([S:12][CH3:11])[N:7]=[N:6][C:5]=1[NH2:8]

Komponenten

4

Edukt 2

HCID 4378561Sodium methanethiolateHCID 69919433-Amino-6-chloro-4,5-dimethylpyridazine

Produkt 1

HCID 717426864,5-Dimethyl-6-(methylthio)pyridazin-3-amineAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6-Chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 400 mg, 2.54 mmol, 1.0 eq) and sodium methanethiolate (196 mg, 2.79 mmol, 1.1 eq) in 10.4 mL ethanol were heated for 1 h to 130° C. in a single mode microwave oven. The reaction mixture was partitioned between DCM and water. The organic phase was washed with brine and dried with sodium sulfate. The resulting mixture was filtered through a Whatman filter and the volatile components were removed in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 50 g SNAP cartridge: DCM/ethanol 95/5→DCM/ethanol 4/1) to give 182 mg (21% yield) of the title compound in 50% purity (UPLC, area-%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationThe resulting mixture was filtered through a Whatman
  5. filtrationfilter
  6. customthe volatile components were removed in vacuo
  7. customThe crude mixture was purified via MPLC (Biotage Isolera; 50 g SNAP cartridge: DCM/ethanol 95/5→DCM/ethanol 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-6a9d5310699e40b09e87b81b59e507e5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206185B2

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