2-Chloroethanol → 3(2H)-Pyridazinone, 6-(2-chlorophenoxy)-2-(2-hydroxyethyl)-

HRID 1448943Notes

Reaction equation

HRID 1448943 reaction equation
[Na].[Cl:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9](=[O:12])[NH:10][N:11]=1.Cl[CH2:18][CH2:19][OH:20]>C(O)CCC>[OH:20][CH2:19][CH2:18][N:10]1[C:9](=[O:12])[CH:8]=[CH:7][C:6]([O:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=2[Cl:2])=[N:11]1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 5360545SodiumHCID 20351304HCID 20351304, compound

Product 1

HCID 30525763(2H)-Pyridazinone, 6-(2-chlorophenoxy)-2-(2-hydroxyethyl)-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

2.4 g sodium are dissolved in 100 ml anhydrous 1-butanol and then 30 g 6-(2-chlorophenoxy)-3-pyridazinone prepared in a manner analogous to Example 1 (M.Pt=182° C.) and the reaction mixture is maintained at 100° C. for 1 hour. 9 g 2-chloroethanol are then introduced without application of heat and then the mixture maintained for 9 hours at reflux temperature. The solvent is removed under reduced pressure, 50 ml aqueous N-sodium hydroxide solution are poured onto the residue and the final product is extracted in diethyl ether.

Workup

  1. temperatureof heat
  2. temperaturethe mixture maintained for 9 hours
  3. temperatureat reflux temperature
  4. customThe solvent is removed under reduced pressure, 50 ml aqueous N-sodium hydroxide solution
  5. additionare poured onto the residue
  6. extractionthe final product is extracted in diethyl ether

Sources & evidence

ORD record
ord-c77fcfd75ccf48e4b67021d52cca759f
Source dataset
uspto-grants-1980_02
Patent number
US04188388

Reaction notes

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