Sulfuric Acid → HCID 14303549, compound

HRID 2350966Notes

Reaction equation

HRID 2350966 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10]C.[C:18]1([C:24]#[C:25][C:26]([O:28]CC)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[Al+3].[Cl-].[Cl-].S(=O)(=O)(O)O.[C:40]1(C)C=CC=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:10][C:26](=[O:28])[C:25]([CH3:40])=[C:24]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 14500009HCID 14500009, compound

Product 1

HCID 14303549HCID 14303549, compound

Conditions

Temperature
60 °C

Procedure

Added to 700 ml of toluene were 73.1 g (0.30 mole) of N-(2-chlorophenyl)-1-phenylpropaneimine, 34.8 g (0.20 mole) of ethyl phenylpropiolate and 40.0 g (0.30 mole) of aluminum chloride. The reaction mixture was then heated with stirring as 60° C. for 3 days. After cooling, the reaction mixture was poured into 1000 ml of 2N sulfuric acid, followed by extraction with chloroform. After washing the organic layer with water, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by chromatography on a silica gel column (eluent: ethyl acetate). The crystals obtained were then recrystallized from a 1:2 mixed solvent of chloroform and hexane to give 17.0 g of 1-(2-chlorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone. 1/5HCl having a melting point of 229°-231° C.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with chloroform
  4. washAfter washing the organic layer with water
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)
  8. customThe crystals obtained
  9. customwere then recrystallized from a 1:2 mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-25fd86a7ca7749b0b0eed3b02539756b
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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