Ethylenediamine → N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide

HRID 463358Notes

Reaction equation

HRID 463358 reaction equation
C(O[C:4](=[O:16])[CH:5]([O:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:6])C.[NH2:17][CH2:18][CH2:19][NH2:20]>C(O)C>[NH2:17][CH2:18][CH2:19][NH:20][C:4](=[O:16])[CH:5]([O:7][C:8]1[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=1[Cl:14])[CH3:6]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 13177850Ethyl 2-(2,6-dichlorophenoxy)propanoate

Product 1

HCID 13177851N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamideYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

46.0 g (0.1748 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 212.0 g (3.527 mols) of 1,2-diaminoethane and, after working up, produce 38.0 g (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =-5.8° (c=1/ethanol)

Sources & evidence

ORD record
ord-4e85bf5d297f41329ef4c9b741b894bb
Source dataset
uspto-grants-1985_05
Patent number
US04518783

Reaction notes

Loading…