Epichlorohydrin → HCID 21450254, compound

HRID 1579271Notes

Reaction equation

HRID 1579271 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)[CH:7]=[CH:8][C:9]=1[OH:10])[CH:2]=[CH2:3].[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.N1CCCCC1.[OH-].[Na+]>ClCCl>[CH2:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:18][CH:20]1[O:22][CH2:21]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 1355732836-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 21450254HCID 21450254, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of finely ground 6-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (50 g, 0.22 mole), epichlorohydrin (200 g, 2.2 mole) and piperidine (2 g) was heated on a steam bath for 90 minutes. Evaporation under reduced pressure gave a viscous oil which was dissolved in dichloromethane and stirred for 10 minutes with dilute sodium hydroxide (500 ml). The organic phase was washed with water, dried and evaporated to an oil which slowly solidified. Addition of ethanolether gave 6-[3-allyl-4-(2,3-epoxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (30 g, 47%, m.p. 92.5°-95°C) which was recrystallised from aqueous ethanol to give the pure pyridazinone (m.p. 93.5°-95°C).

Workup

  1. temperaturewas heated on a steam bath for 90 minutes
  2. customEvaporation under reduced pressure
  3. customgave a viscous oil which
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to an oil which
  7. additionAddition of ethanolether

Sources & evidence

ORD record
ord-db0ffb8a2cbb44e197bc2a5b54fc9645
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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