Methyl iodide → HCID 68515216, compound

HRID 639882Notes

Reaction equation

HRID 639882 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[S:13])[NH:8][C:7]([CH3:14])=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].I[CH3:24].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([S:13][CH3:24])=[N:8][C:7]([CH3:14])=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86609502HCID 86609502, compound

Product 1

HCID 68515216HCID 68515216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-methoxy-3-methyl-4-phenylisoquinoline-1(2H)-thione (0.9 g) was combined with 20 mL DMF and 0.33 g of NaH (60% dispersion in mineral oil). The reaction was heated to 60 C and stirred for 30 min. Iodomethane (0.33 mL) was added, and the reaction was stirred overnight at 60 C, then poured into saturated aqueous NH4Cl. The mixture was extracted with EtOAc (3×), then the combined organic solutions were washed with water (1×) and brine (1×), dried (Na2SO4) and concentrated to give 6-methoxy-3-methyl-1-(methylthio)-4phenylisoquinoline, which was used directly in the next step.

Workup

  1. temperatureThe reaction was heated to 60 C
  2. stirringthe reaction was stirred overnight at 60 C
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. washthe combined organic solutions were washed with water (1×) and brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-48d9b70c32b547a1b5b6abb452dfa81c
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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