Methyl iodide → 3-(4-fluoro-phenyl)-5-methylsulfanyl-3,6-dihydro-2H-[1,4]thiazine

HRID 539623Notes

Reaction equation

HRID 539623 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:13][C:12](=[S:14])[CH2:11][S:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15]I>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:13]=[C:12]([S:14][CH3:15])[CH2:11][S:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 582003125-(4-Fluoro-phenyl)-thiomorpholine-3-thione

Product 1

HCID 582002453-(4-fluoro-phenyl)-5-methylsulfanyl-3,6-dihydro-2H-[1,4]thiazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 5-(4-fluoro-phenyl)-thiomorpholine-3-thione (710 mg, 3.2 mmol) in THF (20 mL) was added methyl iodide (1.1 mL, 16.7 mmol). The mixture was stirred at room temperature in the dark 18 hours, then concentrated under reduced pressure to give crude 3-(4-fluoro-phenyl)-5-methylsulfanyl-3,6-dihydro-2H-[1,4]thiazine as a hydroiodide salt, which was used directly in without further purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b894313817a44fa4b5f46975e3e491dc
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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