Ethylenediamine → 1-[(2-Aminoethyl)amino]-3-(2-chlorophenoxy)propan-2-OL

HRID 371382

Reaction equation

HRID 371382 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH2:5]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])[CH:6]1[O:8][CH2:7]1>C(O)C>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:5][CH:6]([OH:8])[CH2:7][NH:3][CH2:2][CH2:1][NH2:4]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 1375002-(2-Chlorophenoxymethyl)oxirane

Product 1

HCID 155809971-[(2-Aminoethyl)amino]-3-(2-chlorophenoxy)propan-2-OL

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

120 g of ethylenediamine are dissolved in 150 ml of ethanol. A solution of 20 g of o-chlorophenyl glycidyl ether ##STR18## in 40 ml of ethanol is added to the above solution, and the mixture is heated under reflux for 20 hours. Excess ethylenediamine and ethanol are then distilled off in vacuo, and the residue is then distilled in vacuo. The N-[3-(o-chlorophenoxy)-2-hydroxy-propyl]-ethylenediamine is thus obtained as an oil which can be distilled at a boiling point of 190° C./0.4 mm. The 4,5-dichloro-pyridazin-3-one used as the starting material is prepared in a known manner by the reaction of muccochloric acid with hydrazine (for example according to K. Dury, Angew. Chemie 77, page 282 (1965).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 20 hours
  3. distillationExcess ethylenediamine and ethanol are then distilled off in vacuo
  4. distillationthe residue is then distilled in vacuo

Sources & evidence

ORD record
ord-9cae3f62934f4295907cc695825102e2
Source dataset
uspto-grants-1985_07
Patent number
US04532239

Linked notes

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