Sodium → HCID 13827865, compound

HRID 235587Notes

Reaction equation

HRID 235587 reaction equation
C[O-].[Na+].[Na].Cl.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[F:16])[C:10]([NH2:12])=[NH:11]>CO>[CH2:8]([C:9]1[CH:10]=[N:11][C:10]([C:9]2[CH:13]=[CH:14][C:15]([F:16])=[C:7]([F:6])[CH:8]=2)=[N:12][CH:13]=1)[CH3:7]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 198078513,4-Difluorobenzene-1-carboximidamide--hydrogen chloride (1/1)

Product 1

HCID 13827865HCID 13827865, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide prepared by dissolving metallic sodium (2.8 g) dissolved in anhydrous methanol (20 cc) were added 3,4-difluorobenzamidine hydrochloride (11.6 g, 0.06 mol) and α-ethyl-β-dimethylaminoacrolein (8.9 g, 0.066 mol), followed by heating the mixture under reflux for 6 hours, thereafter distilling off methanol at the atmospheric pressure, adding toluene (20 cc) to the reaction residue to extract the product, washing the extraction solution with water, drying the toluene layer over anhydrous sodium sulfate, filtering off the drying agent, distilling off toluene, and recrystallizing the residue from ethanol (20 cc) to obtain the objective 5-ethyl-2-(3,4-difluorophenyl)pyrimidine (7.0 g) having a m.p. of 86.6° C. Its 1H-NMR (proton nuclear magnetic resonance) spectra are shown in FIG. 1.

Workup

  1. temperatureby heating the mixture
  2. temperatureunder reflux for 6 hours
  3. distillationdistilling off methanol at the atmospheric pressure
  4. additionadding toluene (20 cc) to the reaction residue
  5. extractionto extract the product
  6. washwashing the extraction solution with water
  7. dry with materialdrying the toluene layer over anhydrous sodium sulfate
  8. filtrationfiltering off the drying agent
  9. distillationdistilling off toluene
  10. customrecrystallizing the residue from ethanol (20 cc)

Sources & evidence

ORD record
ord-ff02f261e438413f986decf4baa1d5e1
Source dataset
uspto-grants-1987_02
Patent number
US04640795

Reaction notes

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