Water → 6-Chloro-3-isothiocyanato-4-methylpyridazine

HRID 1628465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628465
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.[C:10](Cl)(Cl)=[S:11].O.C(OCC)(=O)C>C(=O)(O)[O-].[Na+].O1CCCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]=[C:10]=[S:11])=[C:4]([CH3:9])[CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 123536646-Chloro-4-methylpyridazin-3-amine

Produkt 1

HCID 866328736-Chloro-3-isothiocyanato-4-methylpyridazineAusbeute 8,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-4-methylpyridazin-3-amine (2.86 g, 20.0 mmol) in aqueous sodium bicarbonate (10 mL) and tetrahydrofuran (40 mL) was added thiophosgene (1.69 mL, 22.0 mmol) dropwise at 0° C. After stirring for 1 hr. water and ethyl acetate were added to the mixture and the insoluble materials were filtered off. The filtrate was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (304 mg, 1.64 mmol, 8%) as a pale yellow solid.

Aufarbeitung

  1. filtrationthe insoluble materials were filtered off
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3710feb3e94f49b8a34380b212d05966
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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