Methyl iodide → 5-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271079Notes

Reaction equation

HRID 2271079 reaction equation
[CH3:1][S:2]([NH:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)(=[O:4])=[O:3].[H-].[Na+].I[CH3:20]>C1COCC1>[CH3:20][N:5]([CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223917905-Methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine

Product 1

HCID 223917805-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepineYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.1 g (6.2 mmol) of 5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine in 15 ml of THF was added dropwise to a suspension of 0.23 g (6.2 mmol) of 80 percent sodium hydride in 10 ml of THF. After 2 h at RT, 0.94 g (6.7 mmol) of iodomethane were added and the mixture was stirred overnight at RT. After distilling off the solvent in vacuo, the residue was taken up in EA, and the solution was washed with dilute hydrochloric acid and water, dried over magnesium sulfate and concentrated. Subsequent recrystallization of the product from isopropanol yielded 0.5 g of 5-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine, m.p. 143-145° C.

Workup

  1. distillationAfter distilling off the solvent in vacuo
  2. washthe solution was washed with dilute hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customSubsequent recrystallization of the product from isopropanol

Sources & evidence

ORD record
ord-709884320e994b2db490e34751abb95b
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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