Dichloromethane → HCID 20548489, compound

HRID 2058877Notes

Reaction equation

HRID 2058877 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[CH:7][N:6]([CH3:21])[CH:5]=1)(=[O:3])C.ClN1C(=O)CCC1=O.[Cl:30][CH2:31][Cl:32]>>[Cl:30][CH:31]([Cl:32])[C:1]([C:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)=[CH:7][N:6]([CH3:21])[CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 132018103-Acetyl-1-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one

Product 1

HCID 20548489HCID 20548489, compound

Procedure

A 4.5 g. portion of 3-acetyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone was dissolved in 125 ml. of dichloromethane, and 2 g. of N-chlorosuccinimide was added. The mixture was stirred under reflux for 60 hours. The mixture was then cooled, and washed successively with 150 ml. each of 1 N sodium hydroxide, 1 N hydrochloric acid, and saturated sodium chloride solution. It was then dried over magnesium sulfate, and evaporated under vacuum to obtain a tan solid. The residue was chromatographed on a 350 g. silica gel column, with 1:10 ethyl acetate:dichloromethane as the eluting solvent. The first product off the column was the dichloroacetyl compound of Example 22, m.p. 184°-186° C., of which 0.6 g. was obtained. Nmr analysis in DMSOd6 showed the following peaks: δ8.4 (s, 1H, CHCl2); 7.6-8.3 (m, 6H, aromatic); 3.9 (s, 3H, N--CH3).

Workup

  1. temperatureunder reflux for 60 hours
  2. temperatureThe mixture was then cooled
  3. washwashed successively with 150 ml
  4. dry with materialIt was then dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customto obtain a tan solid
  7. customThe residue was chromatographed on a 350 g
  8. customwas obtained

Sources & evidence

ORD record
ord-93c2d9c201e1486a9ef19056772d2430
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

Loading…