Ethyl bromoacetate → HCID 13306027, compound

HRID 1075155Notes

Reaction equation

HRID 1075155 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[OH-].[K+].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:16]([O:15][C:13]([CH2:12][N:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[N:6][C:5]1=[O:8])=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 1085785-Chloro-2(1H)-pyrimidinone

Product 1

HCID 13306027HCID 13306027, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloropyrimid-2-one (0.02 mol) was added to a stirred solution of KOH (0.02 mol) in ethanol (100 ml) followed by addition of ethyl bromoacetate (0.023 mol). The reaction mixture was heated under reflux for 4 h. The reaction mixture was then evaporated to dryness at reduced pressure and the residue was extracted with chloroform (150 ml). The chloroform extract, after filtration, was washed with aqueous 0.5 N NaOH (2×3 ml) and water (3 ml). Evaporation of the dried (MgSO4) solution left the product which was recrystallized from acetone; yield 39%, m.p. 175°-177° C. (Found: C 44.65; H, 4.17. Calc. for C8H9ClN2O3 : C 44.36; H, 4.19).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. customThe reaction mixture was then evaporated to dryness at reduced pressure
  4. extractionthe residue was extracted with chloroform (150 ml)
  5. extractionThe chloroform extract
  6. filtrationafter filtration
  7. washwas washed with aqueous 0.5 N NaOH (2×3 ml) and water (3 ml)
  8. customEvaporation of the
  9. dry with materialdried (MgSO4) solution
  10. waitleft the product which
  11. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-35ebdc1f2e5746c8a031698b02e9e95c
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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