Dimethyl Sulfate → 5-methoxy-1-tosyl-2,3-dihydro-1H-1-benzazepine

HRID 726696Notes

Reaction equation

HRID 726696 reaction equation
[H-].[Na+].[S:3]([N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17](=[O:24])[CH2:16][CH2:15][CH2:14]1)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(OC)(O[CH3:29])(=O)=O.[Cl-].[NH4+]>CN(C)C=O>[CH3:29][O:24][C:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:13]([S:3]([C:6]2[CH:7]=[CH:8][C:9]([CH3:10])=[CH:11][CH:12]=2)(=[O:4])=[O:5])[CH2:14][CH2:15][CH:16]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

Product 1

HCID 113819095-methoxy-1-tosyl-2,3-dihydro-1H-1-benzazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide was suspended 165 mg of 60% sodium hydride, and 1.0 g of 1-tosyl-2,3,4,5-tetrahydro-1-H-1 -benzazepin-5-one was added to the suspension under ice-cooling, followed by 1 hour of stirring in the ice bath. To this was added dropwise 0.90 ml of dimethyl sulfate, and the mixture was stirred for 30 minutes. After adding ammonium chloride aqueous solution to the reaction solution and subsequently evaporating the solvent, the thus obtained residue was treated with chloroform and water to effect phase separation, and the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was applied to column chromatography, which was eluted with hexane-ethyl acetate (4:1, v/v) to obtain 621 mg of 5-methoxy-1-tosyl-2,3-dihydro-1H-1-benzazepine.

Workup

  1. additionwas added to the suspension under ice-
  2. temperaturecooling
  3. customsubsequently evaporating the solvent
  4. additionthe thus obtained residue was treated with chloroform and water
  5. customphase separation
  6. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. washwas eluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record
ord-19a228057e4c429da16d281f45916afa
Source dataset
uspto-grants-1998_01
Patent number
US05710150

Reaction notes

Loading…