Methyl iodide → HCID 9903958, compound

HRID 2271070Notes

Reaction equation

HRID 2271070 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:21]I>CC(N(C)C)=O>[F:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([N:11]([S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])[CH3:21])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15434529HCID 15434529, compound

Product 1

HCID 9903958HCID 9903958, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 0.81 g (3 mmol) of 3-fluoro-5-(N-ethylsulfonylamino)-6,7,8,9-tetrahydro-5H-benzocycloheptene (Example 1) in 10 ml of DMA was added dropwise under argon to a suspension of 0.12 g (4.1 mmol) of 80 percent sodium hydride in 5 ml of DMA. After stirring at RT for 3 h, 0.63 g (4.5 mmol) of methyliodide was added dropwise and the mixture was stirred overnight at RT. After distilling off the solvent, the residue was treated with water and extracted with EA. The organic phase was concentrated in vacuo after drying over sodium sulfate. 0.64 g of 3-fluoro-5-(N-ethylsulfonyl-N-methylamino)-6,7,8,9-tetrahydro-5H-benzocycloheptene was obtained.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. distillationAfter distilling off the solvent
  3. additionthe residue was treated with water
  4. extractionextracted with EA
  5. concentrationThe organic phase was concentrated in vacuo
  6. dry with materialafter drying over sodium sulfate

Sources & evidence

ORD record
ord-8958c99a7ee34f06985560a64bc25e6f
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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