Sulfuric Acid → HCID 14303763, compound

HRID 2350960Notes

Reaction equation

HRID 2350960 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[N:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:19]1([C:25]#[C:26][C:27]([O:29]CC)=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:25]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:26][C:27](=[O:29])[C:10]=2[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 198477161-(3,4-dichlorophenyl)-N-phenylpropaneimine

Product 1

HCID 14303763HCID 14303763, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 500 ml of toluene were added 6.2 g (0.022 mole) of 1-(3,4-dichlorophenyl)-N-phenylpropaneimine and 3.9 g (0.022 mole) of ethyl phenylpropiolate, followed by addition of 3.6 g (0.023 mole) of aluminum chloride. After heating the reaction mixture with stirring at 60°-70° C. for 4 days under a nitrogen atmosphere, the reaction mixture was poured into 400 ml of 2N sulfuric acid which had been ice-cooled, followed by extraction with dichloromethane. After washing the organic layer with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate). The resulting crystals were recrystallized from a 2:1 mixed solvent of acetone and hexane to afford 1.9 g of 2-(3,4-dichlorophenyl)-3-methyl-1,6-diphenyl-4(1H)-pyridinone having a melting point of 188°-191° C.

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperaturecooled
  3. extractionfollowed by extraction with dichloromethane
  4. washAfter washing the organic layer with water, it
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customSubsequent to removal of the sodium sulfate
  7. distillationthe solvent was distilled off
  8. customthe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)
  9. customThe resulting crystals were recrystallized from a 2:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-b21dcc550dca4a66b231b8071cded242
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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