Acetophenone → 4-(3-Bromophenyl)-2,6-diphenylpyrimidine

HRID 1482168Notes

Reaction equation

HRID 1482168 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)[CH3:11].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:1][C:2]1[CH:3]=[C:4]([C:5]2[CH:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:31]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:30]=2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 765833-BromobenzaldehydeHCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 589432854-(3-Bromophenyl)-2,6-diphenylpyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into a 500-mL three-neck flask were put 18.5 g (100.0 mmol) of 3-bromobenzaldehyde and 12.0 g (100.0 mmol) of acetophenone, the air in the flask was replaced with nitrogen, and 100 mL of ethanol was added. To this mixture, 6.0 g (111.0 mmol) of sodium methoxide suspended in 100 mL of ethanol was added dropwise, and the mixture was stirred at room temperature for 22 hours. After the stirring for the predetermined time, 15.6 g (100.0 mmol) of benzamidine hydrochloride and 8.0 g (200.0 mmol) of sodium hydroxide were added and the mixture was stirred at 70° C. for 3 hours. After the stirring, the mixture was filtered. Water was added to the residue and ultrasonic cleaning was performed. A solid was collected by suction filtration, so that 14.4 g of a white solid was obtained in a yield of 38.0%.

Workup

  1. customInto a 500-mL three-neck flask were put
  2. additionwas added
  3. additionwas added dropwise
  4. stirringthe mixture was stirred at 70° C. for 3 hours
  5. filtrationAfter the stirring, the mixture was filtered
  6. additionWater was added to the residue and ultrasonic cleaning
  7. filtrationA solid was collected by suction filtration, so that 14.4 g of a white solid
  8. customwas obtained in a yield of 38.0%

Sources & evidence

ORD record
ord-6b82820a27454316b0b065166f8c6d18
Source dataset
uspto-grants-2016_08
Patent number
US09412953B2

Reaction notes

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