Glyoxylic Acid → HCID 19760958, compound

HRID 249286Notes

Reaction equation

HRID 249286 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:15]2C(=O)[NH:18][C:17](C)(C)[NH:16]2)[CH:5]=[C:6]([Cl:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.O.[C:24]([OH:28])(=O)[CH:25]=O.[OH:29]S(O)(=O)=O.C(O)(=O)C=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:25][C:24](=[O:28])[NH:18][C:17](=[O:29])[NH:16]2)[CH:5]=[C:6]([Cl:14])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 760Glyoxylic AcidHCID 1118Sulfuric AcidHCID 15620607Glyoxylic acid, monohydrateHCID 19760963HCID 19760963, compound

Product 1

HCID 19760958HCID 19760958, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3 g (8.5 mmol) of 1-[3,5-dichloro-4-(2-pyridyl)phenyl]-3,3-dimethyl-1,2,4-triazolidin-5-one are dissolved in 50 ml of dioxane, and 0.78 g (8.5 mmol) of glyoxylic acid monohydrate and 0.1 ml of concentrated H2SO4 are added. The mixture is initially stirred at room temperature for 2 h and then a further 0.8 g of glyoxylic acid is added. After the reaction mixture has been stirred under reflux for 5 h it is poured onto water and extracted 3 × with ethyl acetate. The solvent is stripped off in vacuo, and the residue is chromatographed on SiO2 with dichloromethane/methanol (95:5). This results in 1.2 g (40% of theory) of the corresponding azauracil.

Workup

  1. stirringAfter the reaction mixture has been stirred
  2. temperatureunder reflux for 5 h it
  3. additionis poured onto water
  4. extractionextracted 3 × with ethyl acetate
  5. customthe residue is chromatographed on SiO2 with dichloromethane/methanol (95:5)
  6. customThis results in 1.2 g (40% of theory) of the corresponding azauracil

Sources & evidence

ORD record
ord-07496cee7c74490e94283cea96fd2d49
Source dataset
uspto-grants-1993_05
Patent number
US05214043

Reaction notes

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