Chloroform → HCID 20548510, compound

HRID 2058874Notes

Reaction equation

HRID 2058874 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]([CH2:21][CH3:22])[CH:5]=1)(=[O:3])C.ClN1C(=O)CCC1=O.[CH:31]([Cl:34])(Cl)[Cl:32]>>[Cl:32][CH:31]([Cl:34])[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]([CH2:21][CH3:22])[CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 20548492HCID 20548492, compound

Product 1

HCID 20548510HCID 20548510, compound

Procedure

A 0.9 g. portion of 3-acetyl-1-ethyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone was combined with 0.8 g. of N-chlorosuccinimide in 125 ml. of chloroform. The mixture was stirred at reflux overnight, and was then cooled, washed with 1 N sodium hydroxide solution and then with saturated sodium chloride solution, and evaporated under vacuum to obtain 0.9 g. of an orange glass. The residue was chromatographed on a 350 g. silica gel column with 1:10 ethyl acetate:chloroform as the eluting solvent. The product-containing fractions were combined and evaporated under vacuum. The residue was then triturated under hexane to obtain 0.25 g. of the desired product, m.p. 108°-110°. Nmr analysis in DMSOd6 showed peaks at δ7.6-8.4 (m, 7H, aromatic and CHCl2); 4.0-4.4 (q, 2H, N--CH2); 1.4-1.6 (t, 3H, CH2CH3).

Workup

  1. temperatureat reflux overnight
  2. temperaturewas then cooled
  3. washwashed with 1 N sodium hydroxide solution
  4. customwith saturated sodium chloride solution, and evaporated under vacuum
  5. customto obtain 0.9 g
  6. customThe residue was chromatographed on a 350 g
  7. customevaporated under vacuum
  8. customThe residue was then triturated under hexane
  9. customto obtain 0.25 g

Sources & evidence

ORD record
ord-df86b728cb084459bdcdcf6a4e623ebd
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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