1H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1) → N-{5-[(4,5-Dihydro-1H-imidazol-2-ylamino)-methyl]-5,6,7,8-tetrahydro-naphthalen-2-yl}-benzenesulfonamide
Reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2.I.CS[C:26]1[NH:27][CH2:28][CH2:29][N:30]=1>C(Cl)Cl>[NH:30]1[CH2:29][CH2:28][N:27]=[C:26]1[NH:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide and 2-methylsulfanyl-4,5-dihydro-1H-imidazole hydroiodide were added to methylene chloride and the reaction mixture was heated to reflux until all of the solvent evaporates. The reaction mixture is heated to 150° C. and then cooled. The resulting mixture is basified by dropwise addition of aqueous NaOH solution, and then purified by preparative liquid chromatography to give N-{5-[(4,5-Dihydro-1H-imidazol-2-ylamino)-methyl]-5,6,7,8-tetrahydro-naphthalen-2-yl}-benzenesulfonamide. 5-[(4,5-Dihydro-1H-imidazol-2-ylamino)-methyl]-5,6,7,8-tetrahydro-napthalene-2-sulfonic acid phenylamide may be similarly prepared.
Workup
- temperaturethe reaction mixture was heated
- temperatureto reflux until all of the solvent
- customevaporates
- temperaturecooled
- additionThe resulting mixture is basified by dropwise addition of aqueous NaOH solution
- custompurified by preparative liquid chromatography
Sources & evidence
- ORD record
- ord-6ade000977d04fdc804334d334413ba1
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531577B2
Reaction notes
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