Ethylenediamine → 2,3-Dichloro-N-[2-(3-{2-[4-(4,5-dihydro-1H-imidazol-2-yl) phenyl]ethyl}-2-oxoimidazolidin-1-yl)ethyl]-N-methylbenzenesulphonamide hydrochloride

HRID 1591756Notes

Reaction equation

HRID 1591756 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[C:17]1=[O:31])[CH3:13])(=[O:11])=[O:10].[CH2:32](N)[CH2:33][NH2:34].[S]>O>[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[NH:34][CH2:33][CH2:32][N:30]=3)=[CH:27][CH:28]=2)[C:17]1=[O:31])[CH3:13])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 694246682,3-dichloro-N-(2-{3-[2-(4-cyanophenyl)ethyl]-2-oxoimidazolidin-1-yl}ethyl)-N-methylbenzenesulphonamide

Product 1

HCID 694229602,3-Dichloro-N-[2-(3-{2-[4-(4,5-dihydro-1H-imidazol-2-yl) phenyl]ethyl}-2-oxoimidazolidin-1-yl)ethyl]-N-methylbenzenesulphonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 137 mg (0.29 mmol) of 2,3-dichloro-N-(2-{3-[2-(4-cyanophenyl)ethyl]-2-oxoimidazolidin-1-yl}ethyl)-N-methylbenzenesulphonamide, 2 ml of ethylenediamine and 4.6 mg (0.14 mmol) of sulphur was stirred at 100° C. for two hours. Water was then added, and the mixture was extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol/NH3 13:1:0.1 to 8:1:0.1). Using etheral hydrochloric acid, the product was then converted into the hydrochloride and freeze-dried.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40b7d3b4905546ae83aed4274c92ce92
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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