4,5-Dichloro-3-hydroxypyridazine → N-[3-(o-chlorophenoxy)-2-hydroxypropyl]-N'-[4-chloro-3-oxopyridaz-5-yl]-ethylenediamine hydrochloride

HRID 371381Notes

Reaction equation

HRID 371381 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH:6]([OH:12])[CH2:7][NH:8][CH2:9][CH2:10][NH2:11].[Cl:17][C:18]1[C:19](=[O:25])[NH:20][N:21]=[CH:22][C:23]=1Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH:6]([OH:12])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:23]1[CH:22]=[N:21][NH:20][C:19](=[O:25])[C:18]=1[Cl:17]

Participants

4

Reactant 2

HCID 732474,5-Dichloro-3-hydroxypyridazineHCID 155809971-[(2-Aminoethyl)amino]-3-(2-chlorophenoxy)propan-2-OL

Product 1

HCID 15580998N-[3-(o-chlorophenoxy)-2-hydroxypropyl]-N'-[4-chloro-3-oxopyridaz-5-yl]-ethylenediamine hydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4.9 g of N-[3-(o-chlorophenoxy)-2-hydroxy-propyl]-ethylenediamine ##STR15## are dissolved in 50 ml of ethanol. A solution of 3.3 g of 4,5-dichloropyridazin-3-one ##STR16## in 50 ml of ethanol is added to the above solution, and the mixture is then heated under reflux for 12 hours. The mixture is then concentrated in vacuo, the residue is digested with a little ethyl acetate and decanted off from the ethyl acetate, and the residue is finally recrystallised from ethanol. The N-[3-(o-chlorophenoxy)-2-hydroxypropyl]-N'-[4-chloro-3-oxopyridaz-5-yl]-ethylenediamine hydrochloride ##STR17## is thus obtained.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated in vacuo
  4. customdecanted off from the ethyl acetate
  5. customthe residue is finally recrystallised from ethanol

Sources & evidence

ORD record
ord-a15f75c8df9f41408cae84706636688f
Source dataset
uspto-grants-1985_07
Patent number
US04532239

Reaction notes

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