Sulfuric Acid → HCID 14303861, compound

HRID 2350962Notes

Reaction equation

HRID 2350962 reaction equation
Cl[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][C:13]=1Cl)[CH2:10]C.[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-:32].[Al+3].[Cl-:34].[Cl-].S(=O)(=O)(O)O.[C:41]1(C)C=CC=CC=1>>[Cl:32][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:27](=[O:29])[C:26]([CH3:41])=[C:25]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=1[Cl:34]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 6451240Aluminum(III) ChlorideHCID 19847717HCID 19847717, compound

Product 1

HCID 14303861HCID 14303861, compound

Conditions

Temperature
60 °C

Procedure

To 300 ml of toluene were added 6.2 g (0.022 mole) of N,1-bis(2-chlorophenyl)propaneimine, 3.9 g (0.022 mole) of ethyl phenylpropiolate and 3.6 g (0.027 mole) of aluminum chloride. After heating the reaction mixture with stirring at 60° C. for 4 days, the reaction mixture was poured into 500 ml of 2N sulfuric acid, 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 subjected to column chromatography (eluent: ethyl acetate) to obtain two types of atrop-isomers of 1,2-bis(2-chlorophenyl)-3-methyl-6-phenyl-4(1H)-pyridinone, namely, 0.6 g of Compound 335 and 0.2 g of Compound 336, of which the melting points were 205°-207° C. and 232°-234° C., respectively.

Workup

  1. temperatureAfter heating the reaction mixture
  2. extractionfollowed by extraction with dichloromethane
  3. washAfter washing the organic layer with water, it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customSubsequent to removal of the sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3500a6576efd4e9a8a6f402df0dd6599
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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