Toluene → HCID 69798198, compound

HRID 585472Notes

Reaction equation

HRID 585472 reaction equation
[N:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]([C:10]([OH:12])=O)=[N:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:17][N:18]([CH3:21])C=O.[C:22]1(C)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:17]([N:18]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]([C:4]1[CH:5]=[C:6]([C:7]([OH:9])=[O:8])[N:1]=[CH:2][N:3]=1)=[O:12])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 239360pyrimidine-4,6-dicarboxylic acid

Product 1

HCID 69798198HCID 69798198, compound

Conditions

Temperature
10 °C

Procedure

1.7 g of pyrimidine-4,6-dicarboxylic acid are suspended in 20 ml of toluene and 2.4 g of thionyl chloride and 0.2 ml of dimethylformamide are added. The mixture is heated to reflux until it is no longer possible to observe any gas evolution (about 3 hours (h)). About 5 ml of solvent are distilled off and the mixture is then cooled down to from 0 C to 10° C. and 2.7 g of benzylamine, dissolved in 10 ml of toluene, are added. The solution is slowly heated to room temperature, then stirred at room temperature for 12 hours and evaporated down to dryness. The residue is taken up in 50 ml of methylene chloride and the solution is extracted 3 times by shaking with saturated sodium hydrogen carbonate solution; the organic phase is washed with water, dried with magnesium sulfate and evaporated.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux until it
  3. customany gas evolution (about 3 hours (h))
  4. distillationAbout 5 ml of solvent are distilled off
  5. dissolution2.7 g of benzylamine, dissolved in 10 ml of toluene
  6. additionare added
  7. temperatureThe solution is slowly heated to room temperature
  8. customevaporated down to dryness
  9. extractionthe solution is extracted 3 times
  10. stirringby shaking with saturated sodium hydrogen carbonate solution
  11. washthe organic phase is washed with water
  12. dry with materialdried with magnesium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-65789242fdac4ceea1d7f584b1569bb8
Source dataset
uspto-grants-2005_08
Patent number
US06933298B2

Reaction notes

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