Methanol → 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic Acid

HRID 23418

Reaction equation

HRID 23418 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.C[Si]([O:20][S:21](Cl)(=[O:23])=[O:22])(C)C.CO>ClC(Cl)C>[NH:3]1[CH2:4][CH2:5][N:1]=[C:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([S:21]([OH:23])(=[O:22])=[O:20])=[CH:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 78059Trimethylsilyl chlorosulphateHCID 225740011-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-1H-indole

Product 1

HCID 225740321-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic Acid

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-1H-indole (1.0 g, 4.243 mmol) was dissolved/suspended in dichloroethane (120 ml) and cooled in ice under a nitrogen atmosphere. Trimethylsilylchlorosulfonate (0.654 ml, 0.801 g, 4.243 mmol) was added to the cooled solution dropwise with stirring. The mixture was allowed to warm up to room temperature with stirring, and stirring was continued overnight. Methanol (20 mL) was then added, followed by stirring at room temperature for 20 minutes. The mixture was then rotovapped to dryness. The crude product was recrystallized from MeOH/EtOAc as the hydrochloride salt of 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic acid.

Workup

  1. temperaturecooled in ice under a nitrogen atmosphere
  2. stirringwith stirring
  3. stirringstirring
  4. stirringby stirring at room temperature for 20 minutes
  5. customThe crude product was recrystallized from MeOH/EtOAc as the hydrochloride salt of 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic acid

Sources & evidence

ORD record
ord-d6b16d7c07814c4788a5b54d5ffb8990
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Linked notes

Loading…