Sodium sulfate decahydrate → 1-[3-Chloro-5-(methylsulfanyl)phenyl]methanamine hydrochloride

HRID 1015722

Reaktionsgleichung

Reaktionsgleichung von HRID 1015722
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([S:16][CH3:17])[CH:15]=1)[C:11]#[N:12].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[ClH:7].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:11][NH2:12])[CH:13]=[C:14]([S:16][CH3:17])[CH:15]=1

Komponenten

5

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 668786863-Chloro-5-(methylthio)benzonitrile

Produkt 1

HCID 668778401-[3-Chloro-5-(methylsulfanyl)phenyl]methanamine hydrochlorideAusbeute 143,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(Step 2) To a suspension of lithium aluminum hydride (0.79 g) in tetrahydrofuran (200 ml) was added 3-chloro-5-(methylsulfanyl)benzonitrile obtained in Step 1 (3.2 g) at 0° C. The mixture was stirred at room temperature for 3 hr, and treated with sodium sulfate 10 hydrate. The mixture was stirred at room temperature for 30 min, and the inorganic substance was filtered off through celite. The filtrate was concentrated under reduced pressure. The residue was dissolved in methanol, and 4N hydrogen chloride-ethyl acetate solution (5 ml) was added. The mixture was crystallized from methanol-ethyl acetate, and the obtained crystals were washed with ethyl acetate to give 1-[3-chloro-5-(methylsulfanyl)phenyl]methanamine hydrochloride (2.8 g).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. filtrationthe inorganic substance was filtered off through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol
  5. addition4N hydrogen chloride-ethyl acetate solution (5 ml) was added
  6. customThe mixture was crystallized from methanol-ethyl acetate
  7. washthe obtained crystals were washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1afe518b5e9346fdaee47126a1c9bd8e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985862B2

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