Benzaldehyde → HCID 21075637, compound

HRID 1373778Notes

Reaction equation

HRID 1373778 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[C:9](=[N:18]\O)/[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:25].[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:25]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:18][C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 517165Ammonium AcetateHCID 136148285HCID 136148285, compound

Product 1

HCID 21075637HCID 21075637, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (Z)-1-(4-fluorophenyl)-2-(hydroxyimino)-2-(2-(methylthio)pyrimidin-4-yl)ethanone (0.5 g), ammonium acetate (2.7 g) and benzaldehyde (0.2 g) in acetic acid (11 mL) are heated under reflux for 4 h, cooled to room temperature and the majority of the solvent evaporated. The residue is partitioned between ice-cold saturated aqueous sodium hydrogen carbonate and ethyl acetate. The layers are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and the solvent evaporated. The residue is dissolved in methanol (8 mL). This solution is treated with a solution of titanium (III) choride in hydrochloric acid (0.44 mL, 15 wt %, 20–30% hydrochloric acid), followed by stirring at room temperature for 3 h and solvent evaporation. The residue is partitioned between ice-cold saturated aqueous sodium hydrogen carbonate and ethyl acetate, then the layers are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered, the solvent evaporated and the residue purified by chromatography to give the title compound, 75 (0.15 g).

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 4 h
  3. customthe majority of the solvent evaporated
  4. customThe residue is partitioned between ice-cold saturated aqueous sodium hydrogen carbonate and ethyl acetate
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. dissolutionThe residue is dissolved in methanol (8 mL)
  11. additionThis solution is treated with a solution of titanium (III) choride in hydrochloric acid (0.44 mL, 15 wt %, 20–30% hydrochloric acid)
  12. customsolvent evaporation
  13. customThe residue is partitioned between ice-cold saturated aqueous sodium hydrogen carbonate and ethyl acetate
  14. customthe layers are separated
  15. extractionthe aqueous phase is extracted with ethyl acetate
  16. dry with materialThe combined organic phases are dried over sodium sulfate
  17. filtrationfiltered
  18. customthe solvent evaporated
  19. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-c92b025f7ca54e35915f5e8742550944
Source dataset
uspto-grants-2007_01
Patent number
US07163945B2

Reaction notes

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