Sulfuric Acid → HCID 14303555, compound

HRID 845300

Reaction equation

HRID 845300 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10]C)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:22]1([C:28]#[C:29][C:30]([O:32]CC)=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.S(=O)(=O)(O)O.[C:40]1(C)C=CC=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][C:30](=[O:32])[C:29]([CH3:40])=[C:28]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 14726141HCID 14726141, compound

Product 1

HCID 14303555HCID 14303555, compound

Procedure

To 300 ml of toluene were added 9.1 g (0.040 mole) of N-(4-fluorophenyl)-1-phenylpropaneimine, 4.7 g (0.035 mole) of aluminum chloride and 5.2 g (0.030 mole) of ethyl phenylpropiolate, followed by refluxing the resultant mixture for 5 hours. Thereafter, the reaction mixture was poured into 500 ml of 2N sulfuric acid which had been ice-cooled, followed by extraction with chloroform. After washing the organic layer with water, the organic layer wad 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: 1:50 mixed solvent of methanol and chloroform). The resultant crystals were recrystallized from a 1:1 mixed solvent of acetone and hexane to give 1.0 g of 1-(4-fluorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 256°-259° C.

Workup

  1. temperaturecooled
  2. extractionfollowed by extraction with chloroform
  3. washAfter washing the organic layer with water
  4. dry with materialthe organic layer wad dried over anhydrous sodium sulfate
  5. customSubsequent to removal of the sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by chromatography on a silica gel column (eluent: 1:50 mixed solvent of methanol and chloroform)
  8. customThe resultant crystals were recrystallized from a 1:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-3004a3c027a243cea900b2bf096adce4
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Linked notes

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