Ethylene Glycol → 2-[(3,6-Dichloro-4-pyridazinyl)oxy]ethanol

HRID 15169

Reaction equation

HRID 15169 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[Cl:7][C:8]1[N:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1Cl.BrC1C(Cl)=C(Cl)N=NC=1>O1CCCC1>[Cl:7][C:8]1[N:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[O:3][CH2:2][CH2:1][OH:4]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 951233,4,6-TrichloropyridazineHCID 86614155Bromo-dichloropyridazine

Product 1

HCID 817635472-[(3,6-Dichloro-4-pyridazinyl)oxy]ethanolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethylene glycol (55 ml) in tetrahydrofuran (200 ml) was treated at around 0° C. (ice bath cooling) with sodium hydride (60% dispersion in oil, 5.9 g) over 40 minutes. After the addition was complete, 3,4,6-trichloropyridazine (27 g) containing isomers of bromo-dichloropyridazine as impurity was added portionwise and washed in with more dry THF (50 ml) and the mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. The mixture was concentrated (to ⅓ volume) then diluted with aqueous sodium bicarbonate solution and extracted with chloroform (5×) and ethyl acetate (3×). The combined organic extracts were washed with water, dried over sodium sulphate and evaporated and the solids filtered off and washed with CHCl3 (×3) and dried in a vacuum oven overnight at 40° C. affording a white solid (25.5 g, 83%), containing some bromo-derivative (10-15%).

Workup

  1. additionAfter the addition
  2. additionwas added portionwise
  3. washwashed in with more dry THF (50 ml)
  4. customat room temperature
  5. customovernight
  6. concentrationThe mixture was concentrated (to ⅓ volume)
  7. additionthen diluted with aqueous sodium bicarbonate solution
  8. extractionextracted with chloroform (5×) and ethyl acetate (3×)
  9. washThe combined organic extracts were washed with water
  10. dry with materialdried over sodium sulphate
  11. customevaporated
  12. filtrationthe solids filtered off
  13. washwashed with CHCl3 (×3)
  14. customdried in a vacuum oven overnight at 40° C.

Sources & evidence

ORD record
ord-689cf38eecdb401b8d95ebc27ee19dc3
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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