Epichlorohydrin → HCID 20360773, compound

HRID 1579277Notes

Reaction equation

HRID 1579277 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.N1CCCCC1.[OH-].[Na+]>ClCCl>[O:20]1[CH2:19][CH:18]1[CH2:16][O:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 20360783HCID 20360783, compound

Product 1

HCID 20360773HCID 20360773, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of powdered 6-(3-hydroxy-4-methylphenyl)-4,5-dihydro-3(2H)-pyridazinone (5.0 g, 0.024 mole), epichlorohydrin (19.3 ml, 0.24 mole), and piperidine (0.2 ml) was heated on a steam bath for 1 hour. Evaporation of the solution under reduced pressure gave an oil which was dissolved in a small volume of dichloromethane and stirred with dilute sodium hydroxide solution (15 ml). The organic phase was washed with water, dried, and evaporated to an oil which under reduced pressure gave a solid, 6.2 g, 98%. Trituration with ethanol-ether gave crude 6-[3-(2,3-epoxypropoxy)-4-methylphenyl]-4,5-dihydro-3(2H)-pyridazinone 4.81 g, 76%, m.p. 128°-132°C. Purification, by recrystallisation from ethanol, or by column chromatography (silica, chloroform) gave the pure epoxide, m.p. 140°-142.5°C.

Workup

  1. temperaturewas heated on a steam bath for 1 hour
  2. customEvaporation of the solution under reduced pressure
  3. customgave an oil which
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated to an oil which under reduced pressure
  7. customgave a solid, 6.2 g, 98%

Sources & evidence

ORD record
ord-c242e73a639040ce976f1cf9f3d9d677
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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