Potassium Carbonate → HCID 69107146, compound

HRID 1510925Notes

Reaction equation

HRID 1510925 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]=[C:11]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:12]([NH2:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:33])=[CH:4][C:3]=1[N:10]=[C:11]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 69106729HCID 69106729, compound

Product 1

HCID 69107146HCID 69107146, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.5 g of the obtained 2-(2,4-dichloro-5-hydroxyphenylimino)-2-(pyrrolidine-1-yl)acetamide was dissolved in 50 ml of acetonitrile and 0.25 g of potassium carbonate was then added and the entire mixture was heated to reflux for 1 hour. 0.37 g of ethyl 2-bromopropionate was added to the resulting reaction solution and further heated to reflux for 1 hour. Insolubles were removed from the resultant reaction solution by filtration and the concentrate obtained by evaporating solvents from the filtrate by evaporation under reduced pressure was purified by silica gel column chromatography to obtain 0.37 g of 2-[2,4-dichloro-5-(1-ethoxycarbonylethoxy)phenylimino]-2-(pyrrolidine-1-yl)acetamide (1-3) (yield 55%). m.p. 160-163° C.

Workup

  1. temperaturethe entire mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturefurther heated
  4. temperatureto reflux for 1 hour
  5. customInsolubles were removed from the resultant
  6. customreaction solution
  7. filtrationby filtration
  8. customthe concentrate obtained
  9. customby evaporating solvents from the filtrate
  10. customby evaporation under reduced pressure
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f7b0e3ec491543a79998880f21f77e90
Source dataset
uspto-grants-2012_07
Patent number
US08212050B2

Reaction notes

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