Chloroacetic Acid → Uracil-5-ylacetic acid

HRID 1281077Notes

Reaction equation

HRID 1281077 reaction equation
[NH:1]1[CH:8]=[C:7]([CH2:9][C:10]([O:12]CC)=[O:11])[C:5](=[O:6])[NH:4][C:2]1=S.ClCC(O)=[O:18].Cl>O>[NH:1]1[CH:8]=[C:7]([CH2:9][C:10]([OH:12])=[O:11])[C:5](=[O:6])[NH:4][C:2]1=[O:18]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 3659581Ethyl (4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)acetate

Product 1

HCID 298035Uracil-5-ylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl (2-thiouracil-5-yl)acetate (33, 7.8 g, 36 mmol) was mixed with chloroacetic acid (1.9 g, 20 mmol) and water (47 ml) and refluxed for 2 hours. Concentrated hydrochloric acid (22 ml) was added and the reaction mixture was refluxed overnight. The reaction mixture was filtered and the precipitate was washed once with water and dried. The procedure was repeated with the precipitate in place of 8 yielding 4.19 g (68%) of the title compound as a white solid. 1H-NMR (DMSO-d6/TMS): 2=3.13 (s, 2H, CH2COO); 7.35 (d, 1H, J=6.5 Hz, H-6); 10.74 (m, 1H, H-1); 11.09 (s, 1H, H-3); 12.20 (br, 1H, COOH). 13C-NMR (DMSO-d6/TMS): δ=31.3 (CH2COO); 106.6 (C-5); 139.7 (C-6); 151.2 (C-2); 164.0 (C-4); 171.9 (COOH).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturethe reaction mixture was refluxed overnight
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate was washed once with water
  5. customdried

Sources & evidence

ORD record
ord-8f8ff3d0fb3842aa9caa3190ccf5cae0
Source dataset
uspto-grants-2002_09
Patent number
US06451968B1

Reaction notes

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