Epichlorohydrin → HCID 20360753, compound

HRID 596685Notes

Reaction equation

HRID 596685 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 (21.6g, 0.11mole), epichlorohydrin (90ml, 1.1 mole), and piperidine (1 ml) 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 (27g, 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. (Found: C, 63.96; H, 5.70; N, 11.43: M+, 246. C13H 14 N2O3 requires: C, 63.39; H, 5.73; N, 11.38%. M, 246).

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 (27g, 96%)
  7. customPurification on a silica column
  8. washby elution with chloroform

Sources & evidence

ORD record
ord-37efc84f040c40b497f16b84b2c4abb9
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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