Dimethylformamide → 3,5-diphenyl-4(1H)-pyridone

HRID 261774

Reaction equation

HRID 261774 reaction equation
[C:1]1([CH2:7][C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]([NH:19][CH:20](NC=O)NC=O)=O.CN(C)C=O>O>[C:1]1([C:7]2[C:8](=[O:16])[C:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:20][NH:19][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 75931,3-Diphenyl-2-propanoneHCID 78505N,N',N''-Methylidynetrisformamide

Product 1

HCID 124666803,5-diphenyl-4(1H)-pyridone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. temperatureThe mixture was then cooled to approximately room temperature
  3. customThe precipitated solids were separated by filtration
  4. filtrationThe chloroform was then filtered
  5. washthe solids remaining were washed first with water

Sources & evidence

ORD record
ord-2a7aa077b06e428d88b89725156bd94f
Source dataset
uspto-grants-1979_05
Patent number
US04152136

Linked notes

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