Dimethylformamide → 3,5-Bis(3-chlorophenyl)-1-methylpyridin-4(1H)-one

HRID 261775Notes

Reaction equation

HRID 261775 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.C(Cl)(Cl)=O.[Cl:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18](=[O:27])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH:14]=[CH:15][CH:16]=1.CN>C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[C:18](=[O:27])[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[CH:3][N:2]([CH3:5])[CH:1]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 6371PhosgeneHCID 233457391,3-Bis(3-chlorophenyl)propan-2-one

Product 1

HCID 128792643,5-Bis(3-chlorophenyl)-1-methylpyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The aminoformylating reagent was made by adding 30 g. of dimethylformamide dropwise to 20 g. of phosgene in 150 ml. of chloroform at 0° C. A 10 g. portion of 1,3-bis(3-chlorophenyl)-2-propanone in 50 ml. of chloroform was then added. The mixture was stirred for 3 hours, after which 50 ml. of 40% aqueous methylamine was added. Chloroform was then evaporated from the mixture, and 200 ml. of ethanol and 50 ml. of additional 40% aqueous methylamine were added. The mixture was then stirred under reflux overnight. In the morning, the product was extracted as described in the example above, and chromatographed on a silica gel column with ethyl acetate containing successively larger quantities of methanol. The product, 3,5-bis(3-chlorophenyl)-1-methyl-4(1H)-pyridone, 0.85 g., melted at 164°-167° C.

Workup

  1. additionby adding 30 g
  2. customat 0° C
  3. customChloroform was then evaporated from the mixture, and 200 ml
  4. additionof additional 40% aqueous methylamine were added
  5. stirringThe mixture was then stirred
  6. temperatureunder reflux overnight
  7. extractionIn the morning, the product was extracted
  8. customchromatographed on a silica gel column with ethyl acetate containing successively larger quantities of methanol

Sources & evidence

ORD record
ord-7d7a3004e90a47bca0786162ce416c32
Source dataset
uspto-grants-1979_05
Patent number
US04152136

Reaction notes

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