Chloroacetic Acid → (6-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetic acid

HRID 1399557Notes

Reaction equation

HRID 1399557 reaction equation
ClCC(O)=[O:4].[CH3:6][C:7]1[NH:12][C:11](=S)[NH:10][C:9](=[O:14])[C:8]=1[CH2:15][C:16]([OH:18])=[O:17]>>[CH3:6][C:7]1[NH:12][C:11](=[O:4])[NH:10][C:9](=[O:14])[C:8]=1[CH2:15][C:16]([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 300Chloroacetic AcidHCID 686779HCID 686779, compound

Product 1

HCID 743202(6-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetic acidYield 77%

Procedure

A 10% aq chloroacetic acid solution (150 mL; 159 mmol) was added to 2-(6-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetic acid (7.3 g; 36.5 mmol). The mixture was stirred under reflux for 24 h and cooled in an ice-bath. The formed solid was collected by filtration, washed with water and dried under reduced pressure to give 5.17 g (77%) of the title compound as a white solid.

Workup

  1. temperatureunder reflux for 24 h
  2. temperaturecooled in an ice-bath
  3. filtrationThe formed solid was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d18a529e13f245a49175b89a47cf5f7e
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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