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

HRID 586947Notes

Reaction equation

HRID 586947 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][NH:29][CH3:30]>ClCCl.CO>[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])[N:29]([CH3:30])[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 674DimethylamineHCID 24638Chlorosulfonic acid2×HCID 22329106methyl 7-bromo-1-phenyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22328934methyl 7-bromo-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (10 ml) was dissolved methyl 7-bromo-1-phenyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.4 g). Under ice-cooling, to the solution was added dropwise chlorosulfonic acid (0.74 ml). The mixture was stirred at room temperature for 30 minutes and, to the mixture was additionally added chlorosulfonic acid (0.37 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was added dropwise to 2M dimethylamine solution in methanol (35 ml) under ice-cooling, and the mixture was stirred overnight. The solvent was evaporated and, to the residue was added water, and the mixture was 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,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.37 g) as yellow crystals.

Workup

  1. temperatureUnder ice-cooling, to the solution
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. temperaturecooling
  4. stirringthe mixture was stirred overnight
  5. customThe solvent was evaporated and, to the residue
  6. additionwas added water
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-89909b8832cc4b4c93de98bf265b9e79
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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