Pyridine → HCID 58175621, compound

HRID 2041825Notes

Reaction equation

HRID 2041825 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5]([NH2:6])=[C:4]([CH2:11][CH3:12])[CH:3]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[Br:1][C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5]([NH:6][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH2:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 6114524-Bromo-2,6-diethylaniline

Product 1

HCID 58175621HCID 58175621, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromo-2,6-diethylaniline (5.48 g, 24 mmol) in dichloromethane was added and stirred under nitrogen. Pyridine (5.7 g, 72.1 mmol) was added followed by benzoyl chloride (4.39 g, 31.2 mmol). The reaction was stirred for 1 h. The reaction was diluted with dichloromethane, washed with 10% sodium hydroxide solution, 1N HCl, and dried over magnesium sulfate, filtered, and evaporated. The residue was pre-absorbed onto Celite and purified by column chromatography. The column was eluted with 40 to 100% dichloromethane/hexanes. 7.64 g (96% yield) of product was obtained after purification.

Workup

  1. stirringThe reaction was stirred for 1 h
  2. washwashed with 10% sodium hydroxide solution, 1N HCl
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was pre-absorbed onto Celite
  7. custompurified by column chromatography
  8. washThe column was eluted with 40 to 100% dichloromethane/hexanes

Sources & evidence

ORD record
ord-9475b54e0c7c4432a9992d434555a948
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

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