1H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1) → (6-benzenesulfonyl-naphthalen-1-ylmethyl)-(4,5-dihydro-1H-imidazol-2-yl)-amine

HRID 1715059Notes

Reaction equation

[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH2:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I.CS[C:25]1[NH:26][CH2:27][CH2:28][N:29]=1>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH:21][C:25]2[NH:29][CH2:28][CH2:27][N:26]=2)=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine 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 (6-benzenesulfonyl-naphthalen-1-ylmethyl)-(4,5-dihydro-1H-imidazol-2-yl)-amine.

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-62312c1ce61d428ab0e3c29b77c4f2f9
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799797B2

Reaction notes

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