Butyl iodide → 7-Chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271084Notes

Reaction equation

HRID 2271084 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][CH:7](NS(CC)(=O)=O)[C:6]=2[CH:18]=1.[H-].[Na+].C(I)CCC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 223917937-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine

Product 1

HCID 1317230517-Chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.8 g (2.6 mmol) of 7-chloro-9-methyl-5-(N-ethylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine (Example 10c) in 10 ml of DMF was added dropwise under nitrogen to a suspension of 0.1 g (2.7 mmol) of 80 percent sodium hydride in 8 ml of DMF. After stirring at RT for 30 min, 0.68 g (3.7 mmol) of butyl iodide was 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. After washing the organic phase with dil. hydrochloric acid in water, and drying over magnesium sulfate, it was concentrated in vacuo. 0.9 g of 5-N-butyl-N-ethylsulfonylamino)-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine was obtained, m.p. 83-87° 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. washAfter washing the organic phase with dil. hydrochloric acid in water
  6. dry with materialdrying over magnesium sulfate, it
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-9eb08fdf4bc146858a7e141c29720522
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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