Epichlorohydrin → HCID 20360753, compound

HRID 1579274Notes

Reaction equation

HRID 1579274 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl.N1CCCCC1.[OH-].[Na+]>ClCCl>[O:19]1[CH2:18][CH:17]1[CH2:15][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 19884680HCID 19884680, compound

Product 1

HCID 20360753HCID 20360753, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of finely powdered 6-(3-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (21.6 g, 0.11 mole), epichlorohydrin (90 ml, 1.1 mole), and piperidine (1ml) was heated on a steam bath for 90 minutes. Evaporation of the solution under reduced pressure gave an oil which was dissolved in dichloromethane and stirred with dilute sodium hydroxide solution (60 ml). The organic phase was washed with water, dried, and evaporated under reduced pressure to a viscous oil (27 g, 96%). Purification on a silica column by elution with chloroform gave 6-[3-(2,3-epoxypropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone (16.5g, 59%) as an oil which when treated with ether gave a white solid (13.7g, 49%, m.p. 108°-112°C). The pure epoxide, recrystallised from methanol petroleum/ether (b.p. 60°-80°C), had m.p. 110°-112°C.

Workup

  1. temperaturewas heated on a steam bath for 90 minutes
  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 under reduced pressure to a viscous oil (27 g, 96%)
  7. customPurification on a silica column
  8. washby elution with chloroform

Sources & evidence

ORD record
ord-6a8ad5c91fcf4f849a24c26d3bffb320
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

Loading…