Sulfuric Acid → HCID 14303549, compound

HRID 845307Notes

Reaction equation

HRID 845307 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 at 60° C. for 3 days. After cooling, the reaction mixture was poured into 1000 ml of 2N sulfuric acid, followed by extraction withchloroform. 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 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 withchloroform
  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-6aece3ee947347f38f3cff5562ecfe67
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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