Sodium sulfate decahydrate → 1-[5-Chloro-2-(methylsulfanyl)phenyl]methanamine hydrochloride

HRID 447825Notes

Reaction equation

HRID 447825 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:16][CH3:17])=[C:12]([CH:15]=1)[C:13]#[N:14].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]=[CH:10][C:11]([S:16][CH3:17])=[C:12]([CH2:13][NH2:14])[CH:15]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 598456935-Chloro-2-(methylthio)benzonitrile

Product 1

HCID 668779171-[5-Chloro-2-(methylsulfanyl)phenyl]methanamine hydrochlorideYield 146.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Step 2) To a suspension of lithium aluminum hydride (1.41 g) in tetrahydrofuran (300 ml) was added 5-chloro-2-(methylsulfanyl)benzonitrile obtained in Step 1 (5.7 g) at 0° C. The mixture was stirred at room temperature for 3 hr, and treated with sodium sulfate 10 hydrate. The mixture was further stirred at room temperature for 1 hr, 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 (10 ml) was added. The mixture was crystallized from methanol-ethyl acetate to give 1-[5-chloro-2-(methylsulfanyl)phenyl]methanamine hydrochloride (5.11 g).

Workup

  1. stirringThe mixture was further stirred at room temperature for 1 hr
  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 (10 ml) was added
  6. customThe mixture was crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-45383dd027ff48f2a0b70480cd74d890
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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