Sodium Hydroxide → Methanesulfonamide, N-(4-(2-hydroxy-3-((2-(4-(1H-imidazol-1-yl)phenoxy)ethyl)amino)propoxy)phenyl)-, monohydrochloride, (+-)-

HRID 728837Notes

Reaction equation

HRID 728837 reaction equation
[ClH:1].Cl.[N:3]1([C:8]2[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14][NH2:15])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.[OH-].[Na+].[O:20]1[CH2:22][CH:21]1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=1>CO.O>[ClH:1].[OH:20][CH:21]([CH2:22][NH:15][CH2:14][CH2:13][O:12][C:11]1[CH:16]=[CH:17][C:8]([N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[CH:9][CH:10]=1)[CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 145556582-[4-(1H-Imidazol-1-yl)phenoxy]ethanamine dihydrochlorideHCID 147398742-[(4-(Methanesulfonamido)phenoxy)methyl]oxirane

Product 1

HCID 3079339Methanesulfonamide, N-(4-(2-hydroxy-3-((2-(4-(1H-imidazol-1-yl)phenoxy)ethyl)amino)propoxy)phenyl)-, monohydrochloride, (+-)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.3 g (0.008 mol) of 2-[4-(1H-imidazol-1-yl)phenoxy]ethanamine dihydrochloride in 100 ml of methanol add a solution of 0.66 g of sodium hydroxide in 5 mL of water. Stir for 15 minutes. Add 2.0 g (0.008 mol) of N-[4-(oxiranylmethoxy)phenyl]methanesulfonamide and reflux for 16 h. Monitor the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride, methanol, triethylamine, 84:15:1). Remove the solvent in vacuo. Chromatograph the oil on 350 g of silica gel using amixture of methylene chloride:methanol:triethylamine (94:5:1). Combine the fractions containing residue and remove the solvent in vacuo. Dissolve theresidue in methanol and add a solution of hydrogen chloride in methanol. Remove the solvent in vacuo. Recrystallize the salt from acetonitrile:methanol to obtain the title compound.

Workup

  1. temperaturereflux for 16 h
  2. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride, methanol, triethylamine, 84:15:1)
  3. customRemove the solvent in vacuo
  4. additionCombine the fractions containing residue
  5. customremove the solvent in vacuo
  6. dissolutionDissolve
  7. additionin methanol and add a solution of hydrogen chloride in methanol
  8. customRemove the solvent in vacuo
  9. customRecrystallize the salt from acetonitrile

Sources & evidence

ORD record
ord-3b4a6a5f4c23429eba1d80b1e599c8fb
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

Loading…