Chlorosuccinimide → HCID 20548514, compound

HRID 2058876Notes

Reaction equation

HRID 2058876 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:5](=[O:18])[C:4]([C:19](=[O:22])[CH2:20][CH3:21])=[CH:3]1.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:23][CH:20]([CH3:21])[C:19]([C:4]1[C:5](=[O:18])[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)=[CH:7][N:2]([CH3:1])[CH:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1578584(1H)-Pyridinone, 1-methyl-3-(1-oxopropyl)-5-[3-(trifluoromethyl)phenyl]-

Product 1

HCID 20548514HCID 20548514, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 2.7 g. portion of 1-methyl-3-propionyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinone was dissolved in 125 ml. of chloroform, and 2.3 g. of N-chlorosuccinimide was added. The mixture was stirred under reflux overnight, and was then cooled and washed, first with 1 N sodium hydroxide, and then with saturated sodium chloride solution. The organic layer was then dried over magnesium sulfate and evaporated under vacuum to obtain 2.2 g. of a partially crystalline solid. The product was crystallized from diisopropyl ether to obtain 1.2 g. of the desired product, m.p. 129°, dec., showing the following nmr peaks in DMSOd6 : δ7.5-8.4 (m, 6H, aromatic); 5.8-6.2 (q, 1H, CHCl); 1.5-1.6 (d, 3H, CHClCH3); 3.8 (s, 3H, N--CH3).

Workup

  1. temperatureunder reflux overnight
  2. temperaturewas then cooled
  3. washwashed, first with 1 N sodium hydroxide
  4. dry with materialThe organic layer was then dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customto obtain 2.2 g
  7. customThe product was crystallized from diisopropyl ether
  8. customto obtain 1.2 g

Sources & evidence

ORD record
ord-6dbafa9b73e34a239f637e6dcca75420
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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