Ethylenediamine → N-{3-[(2,3-Dichlorobenzenesulphonyl)methylamino]-propyl}-3-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]propionamide

HRID 1591749Notes

Reaction equation

HRID 1591749 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=2[Cl:29])(=[O:21])=[O:20])=[O:12])=[CH:5][CH:4]=1)#[N:2].[CH2:30](N)[CH2:31][NH2:32].[S]>O>[Cl:29][C:23]1[C:24]([Cl:28])=[CH:25][CH:26]=[CH:27][C:22]=1[S:19]([CH2:18][NH:17][CH2:16][CH2:15][CH2:14][NH:13][C:11](=[O:12])[CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]2[NH:32][CH2:31][CH2:30][N:2]=2)=[CH:8][CH:7]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 694217413-(4-Cyanophenyl)-N-{3-[(2,3-dichlorobenzenesulphonyl)methyl-amino]propyl}propionamide

Product 1

HCID 69423023N-{3-[(2,3-Dichlorobenzenesulphonyl)methylamino]-propyl}-3-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]propionamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.7 g (1.54 mmol) of 3-(4-cyanophenyl)-N-{3-[(2,3-dichloro-benzenesulphonyl)methylamino]propyl}propionamide, 3 ml of ethylenediamine and 0.10 g (3.12 mmol) of sulphur was stirred at 100° C. for 15 minutes. Water was then added, and the mixture was extracted with ethyl acetate. The organic extracts were washed with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product obtained in this manner was purified by column chromatography on alumina (mobile phase: dichloromethane/methanol 100:1) and then crystallized from ethyl acetate/diethyl ether.

Workup

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

Sources & evidence

ORD record
ord-54b15a7d84a3498ea76b22af7d8dc7a9
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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