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

HRID 1013987Notes

Reaction equation

HRID 1013987 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:16][CH2:17][CH3:18])=[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][CH2:17][CH3:18])=[C:12]([CH2:13][NH2:14])[CH:15]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 624932485-Chloro-2-(ethylsulfanyl)benzonitrile

Product 1

HCID 668775201-[5-Chloro-2-(ethylsulfanyl)phenyl]methanamine hydrochlorideYield 132.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(Step 2) To a suspension of lithium aluminum hydride (1.7 g) in tetrahydrofuran (300 ml) was added a solution of 5-chloro-2-(ethylsulfanyl)benzonitrile obtained in Step 1 (7.4 g) in tetrahydrofuran (20 ml) 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 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 (15 ml) was added. The mixture was crystallized from methanol-ethyl acetate to give 1-[5-chloro-2-(ethylsulfanyl)phenyl]methanamine hydrochloride (5.89 g).

Workup

  1. stirringThe mixture was further 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 (15 ml) was added
  6. customThe mixture was crystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-0beccb025ed94856853250a65e4a4a19
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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