Methyl iodide → HCID 21699015, compound

HRID 1597162Notes

Reaction equation

HRID 1597162 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7](=[O:12])[CH:8]=[C:9]([SH:11])[S:10][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:17]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7](=[O:12])[CH:8]=[C:9]([S:11][CH3:17])[S:10][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 21699006HCID 21699006, compound

Product 1

HCID 21699015HCID 21699015, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methoxy-2-mercapto-4-oxo-4H-1-benzothiopyran (2.00 g, 8.92 mmol) was dissolved in DMF (15 ml) and gradually added with sodium hydride (505.8 mg, 11.59 mmol) over 30 minutes in the ice bath and under nitrogen atmosphere. After removal of the ice bath and stir for 12 hours, the solution was added with methyl iodide (0.83 ml, 13.37 mmol) and further stirred for 3 hours. The reaction liquid was injected into the cooled aqueous solution (100 ml) of saturated ammonium chloride. The precipitated crude crystals were filtrated and fully washed with water and dried in a desiccator under reduced pressure. The crude crystals were washed with the ether-hexane solution to obtain 1.77 g (yield: 83%) of 7-methoxy-2-methylthio-4-oxo-4H-1-benzothiopyran as light yellow powder.

Workup

  1. customAfter removal of the ice bath
  2. stirringfurther stirred for 3 hours
  3. customThe reaction liquid
  4. customThe precipitated crude crystals
  5. filtrationwere filtrated
  6. washfully washed with water
  7. customdried in a desiccator under reduced pressure
  8. washThe crude crystals were washed with the ether-hexane solution

Sources & evidence

ORD record
ord-5e727570adc748cdb1df9e6cb364f6d0
Source dataset
uspto-grants-2001_09
Patent number
US06294527B1

Reaction notes

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