Reaction equation
[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]=1Participants
Procedure
(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).
Workup
- stirringThe mixture was stirred at room temperature for 30 min
- filtrationthe inorganic substance was filtered off through celite
- concentrationThe filtrate was concentrated under reduced pressure
- dissolutionThe residue was dissolved in methanol
- addition4N hydrogen chloride-ethyl acetate solution (5 ml) was added
- customThe mixture was crystallized from methanol-ethyl acetate
- washthe obtained crystals were washed with ethyl acetate
Sources & evidence
- ORD record
- ord-33810ac449774df88c79fd7ee32adf0e
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985863B2
Linked notes
Loading…