Sulfuric Acid → HCID 14303698, compound

HRID 845305Notes

Reaction equation

HRID 845305 reaction equation
[Cl:1][CH2:2][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].C1([CH:24](C)[C:25](OCC)=[O:26])C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[Cl:1][C:2]1[C:25](=[O:26])[CH:24]=[C:46]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 99643Benzeneacetic acid, alpha-methyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 19847709HCID 19847709, compound

Product 1

HCID 14303698HCID 14303698, compound

Procedure

To 300 ml of toluene were added 7.4 g (0.030 mole) of 2-chloro-N-(2-chlorophenyl)-1-phenylethaneimine, 5.2 g (0.030 mole) of ethyl phenylpropionate and 6.7 g (0.050 mole) of aluminum chloride. The reaction mixture was then heated under reflux for 20 hours under nitrogen atmosphere. After cooling, the reaction mixture was poured into 500 ml of 2N sulfuric acid, followed by extraction with chloroform. After washing the organic layer with 50 ml of a 10% aqueous solution of sodium hydroxide and then with water, it was dried with 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) to yield 3-chloro-1-(2-chlorophenyl)-2,6-diphenyl-4(1H)-pyridinone having a melting point of 230°-233° C.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 20 hours under nitrogen atmosphere
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with chloroform
  5. washAfter washing the organic layer with 50 ml of a 10% aqueous solution of sodium hydroxide
  6. dry with materialwith water, it was dried with anhydrous sodium sulfate
  7. customSubsequent to removal of the sodium sulfate
  8. distillationthe solvent was distilled off
  9. customthe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-c54dd9ee143a4036b0b63f30d0bc3115
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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