Epichlorohydrin → HCID 12899141, compound

HRID 621551Notes

Reaction equation

HRID 621551 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:20][CH:22]2[O:24][CH2:23]2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 12899140HCID 12899140, compound

Product 1

HCID 12899141HCID 12899141, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

20.0 grams of 8-chloro-5-hydroxy-3,4-dihydrocarbostyril and 18 g of potassium carbonate are suspended in 160 ml of isopropyl alcohol, then 40 ml of epichlorohydrin are added and the reaction is carried out at 70°-80° C. for 6 hours. The reaction mixture is concentrated under reduced pressure and the thus-obtained residue is stirred with 100 ml of 2N-sodium hydroxide under cooling conditions. The insoluble matter is separated by filtration, washed with water and dried. The crude crystals are recrystallized from isopropanol to obtain 18.5 g of 8-chloro-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 161°-165° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe insoluble matter is separated by filtration
  3. washwashed with water
  4. customdried
  5. customThe crude crystals are recrystallized from isopropanol

Sources & evidence

ORD record
ord-5e523024c4e9455995b098fbac31eab5
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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