Dimethyl Sulfoxide → 2-Thiouracil-5-carboxylic acid

HRID 482180Notes

Reaction equation

HRID 482180 reaction equation
CC(C)([O-])C.[K+].CS(C)=O.CC[O:13][C:14]([C:16]1[C:22](=[O:23])[NH:21][C:19](=[S:20])[NH:18][CH:17]=1)=[O:15]>CO>[C:14]([C:16]1[C:22](=[O:23])[NH:21][C:19](=[S:20])[NH:18][CH:17]=1)([OH:15])=[O:13]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 735952Ethyl 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 30020412-Thiouracil-5-carboxylic acidYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium tertiary butoxide (43.7 g, 389 mmol) and dimethyl sulfoxide (400 ml) were put in a 2-L egg-plant type flask to make a solution, ethyl 2-thiouracil-5-carboxylate (5.0 g, 25.0 mmol) was slowly added dropwise to the solution, and the mixture was subjected to reaction at room temperature for 1 hour. After the completion of the reaction, methanol (500 ml) was added to the reaction mixture, and the precipitate deposited was filtered. The resultant precipitate was dissolved in water, and hydrochloric acid was added to this solution to give 5-carboxy-2-thiouracil (2.54 g) as a light yellow solid.

Workup

  1. additionwas slowly added dropwise to the solution
  2. customthe mixture was subjected to reaction at room temperature for 1 hour
  3. additionwas added to the reaction mixture
  4. filtrationthe precipitate deposited was filtered
  5. dissolutionThe resultant precipitate was dissolved in water
  6. additionhydrochloric acid was added to this solution

Sources & evidence

ORD record
ord-f896796e32f74b0fb3910bb72187f79d
Source dataset
uspto-grants-1998_08
Patent number
US05795497

Reaction notes

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