Methylamine → methyl 7-bromo-1-(N-methyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586950Notes

Reaction equation

HRID 586950 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=2[CH:22]=1.Cl[S:24]([OH:27])(=O)=[O:25].[CH3:28][NH2:29]>ClCCl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:24](=[O:27])(=[O:25])[NH:29][CH3:28])=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=2[CH:22]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 24638Chlorosulfonic acidHCID 22329106methyl 7-bromo-1-phenyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22329309methyl 7-bromo-1-(N-methyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (20 ml) was dissolved methyl 7-bromo-1-phenyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1 g). Under ice-cooling, to the solution was added dropwise chlorosulfonic acid (0.93 ml). The mixture was stirred at room temperature for 1 hour, and the reaction solution was added dropwise to 40% methylamine solution in water (25 ml) under ice-cooling. The mixture was stirred at room temperature overnight, concentrated and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated to give methyl 7-bromo-1-(N-methyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1 g) as yellow crystals.

Workup

  1. temperatureUnder ice-cooling, to the solution
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature overnight
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1ac3580340e84aeda1e2d052a4f8361e
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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