Citric Acid → HCID 18700276, compound

HRID 2288630Notes

Reaction equation

HRID 2288630 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([O:14]CC)=[O:13])=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 18700275HCID 18700275, compound

Product 1

HCID 18700276HCID 18700276, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Ethyl 2-(5-chloro-6-ethylpyrimidin-4-yloxy)acetate (2.6 g) was dissolved in ethanol (50 ml). A solution containing sodium hydroxide (0.7 g) dissolved in water (10 ml) was added thereto in a dropwise manner, and subsequently the mixture was stirred for an hour at room temperature. After completion of the reaction, water was added to the reaction liquid. Subsequently, the reaction liquid was acidified using citric acid. The organic layer was extracted with ethyl acetate and then was dried over anhydrous magnesium sulfate. The ethyl acetate was removed under reduced pressure. The obtained crystals were washed with hexane to give 1.4 g of the desired product having a melting point of 158° C. to 159° C.

Workup

  1. additionwas added
  2. additionwas added to the reaction liquid
  3. customSubsequently, the reaction liquid
  4. extractionThe organic layer was extracted with ethyl acetate
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe ethyl acetate was removed under reduced pressure
  7. washThe obtained crystals were washed with hexane

Sources & evidence

ORD record
ord-8ce27723acc54d20bd3260f365e14011
Source dataset
uspto-grants-2000_07
Patent number
US06090815

Reaction notes

Loading…