Methyl iodide → 5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271077

Reaction equation

HRID 2271077 reaction equation
[CH2:1]([S:3]([NH:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9][CH2:8]1)(=[O:5])=[O:4])[CH3:2].[H-].[Na+].[CH3:20]I>C1COCC1>[CH2:1]([S:3]([N:6]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9][CH2:8]1)[CH3:20])(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223918085-Ethylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine

Product 1

HCID 154345335-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepineYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g (3.9 mmol) of 5-ethylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine in 15 ml of THF were added dropwise under nitrogen to a suspension of 0.16 g (5.4 mmol) of 80 percent sodium hydride in 10 ml of THF. After stirring at RT for 3 h, 1.6 g (11 mmol) of methyl iodide were added dropwise and the mixture was additionally 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. 1.0 g of 5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepine was obtained, m.p. 122-124° C.

Workup

  1. waitthe mixture was additionally 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-a6dc94c4fe4b4a9fbe05f414a473c68f
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Linked notes

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