Triethylamine → HCID 22008838, compound

HRID 2287347Notes

Reaction equation

HRID 2287347 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].[NH:12]1[CH:17]=[CH:16][C:15](=[O:18])[CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([N:12]1[CH:13]=[CH:14][C:15](=[O:18])[CH2:16][CH2:17]1)=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27568702-bromo-6-chlorobenzoyl chlorideHCID 122236384(1H)-Pyridinone, 2,3-dihydro-

Product 1

HCID 22008838HCID 22008838, compoundYield 399.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-bromo-6-chlorobenzoic acid chloride (0.5 mmol) in dichloromethane (5 ml) was added dropwise to a solution of 2,3-dihydro-4-pyridinone (5.1 mmol, 495 mg) and triethylamine (1.2 ml) in dichloromethane (20 ml). After stirring for 30 minutes, the solution was diluted with water, separated, the aqueous extract further extracted with dichloromethane, the combined organic extracts combined and washed with brine, dried over sodium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 30% ethyl acetate in hexane to yield the title compound as a pale yellow oil (629 mg). MS (+CI) m /z 316 [M+H]+.

Workup

  1. customseparated
  2. extractionthe aqueous extract further
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f765099631d047bf9691ef0644ee968f
Source dataset
uspto-grants-2000_07
Patent number
US06083952

Reaction notes

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