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

HRID 325891Notes

Reaction equation

HRID 325891 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 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

Sources & evidence

ORD record
ord-3a08fc7097a44d909070b63b9c8caf22
Source dataset
uspto-grants-1984_04
Patent number
US04443464

Reaction notes

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