Acetophenone → 4-(4-bromophenyl)-2,6-diphenylpyrimidine

HRID 1482169Notes

Reaction equation

HRID 1482169 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C[O-].[Na+].Cl.[C:23]([NH2:31])(=[NH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>C(O)C>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]2[CH:2]=[C:1]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:31]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:30]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 707414-BromobenzaldehydeHCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 17148994-(4-bromophenyl)-2,6-diphenylpyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into a 300-mL three-neck flask were put 11 mL (94.6 mmol) of acetophenone and 17.9 g (96.7 mmol) of 4-bromobenzaldehyde, and the air in the flask was replaced with nitrogen. To this mixture, 50 mL of ethanol was added and 5.99 g (110.9 mmol) of sodium methoxide suspended in 50 mL of ethanol was added dropwise. The mixture was stirred at room temperature for 5 hours and further stirred at 70° C. for 50 minutes. After the predetermined time elapsed, 15.1 g (96.6 mmol) of benzamidine hydrochloride and 8.03 g (200 mmol) of sodium hydroxide were added and the mixture was stirred at 70° C. for 9 hours. After the predetermined time elapsed, this mixture was suction-filtered, and the obtained residue was dissolved in chloroform and subjected to extraction with water. The obtained organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. This mixture was subjected to gravity filtration, and the solvent was distilled off to give a solid. The obtained solid was washed with ethanol, so that 8.61 g of an objective white solid was obtained in a yield of 22%.

Workup

  1. customInto a 300-mL three-neck flask were put
  2. additionwas added dropwise
  3. stirringfurther stirred at 70° C. for 50 minutes
  4. stirringthe mixture was stirred at 70° C. for 9 hours
  5. filtrationthis mixture was suction-filtered
  6. dissolutionthe obtained residue was dissolved in chloroform
  7. extractionsubjected to extraction with water
  8. washThe obtained organic layer was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. filtrationThis mixture was subjected to gravity filtration
  11. distillationthe solvent was distilled off
  12. customto give a solid
  13. washThe obtained solid was washed with ethanol, so that 8.61 g of an objective white solid
  14. customwas obtained in a yield of 22%

Sources & evidence

ORD record
ord-3c5c96dbf19c403eb342a51f103a1502
Source dataset
uspto-grants-2016_08
Patent number
US09412953B2

Reaction notes

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