N-bromobutanimide → HCID 22648744, compound

HRID 393166Notes

Reaction equation

HRID 393166 reaction equation
[CH2:1]([C:3]1[C:8]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:7][N:6]=[CH:5][N:4]=1)[CH3:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:10]([CH3:11])[C:9]([C:8]1[C:3]([CH2:1][CH3:2])=[N:4][CH:5]=[N:6][CH:7]=1)=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22648740HCID 22648740, compound

Product 1

HCID 22648744HCID 22648744, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

49.2 g (0.30 mol) of 1-(4-ethylpyrimidin-5-yl)propan-1-one was dissolved in 500 ml of carbon tetrachloride, and 53 g (0.30 mol) of N-bromosuccinimide and 0.3 g of azoisobutyronitrile were added, followed by refluxing for 2 hours. After cooling, crystals were removed by filtration, and the filtrate was concentrated and the obtained oily product was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 1:2) to obtain 64.3 g (yield: 89%) of 2-bromo-1-(4-ethylpyrimidin-5-yl)-propan-1-one as yellow liquid.

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter cooling
  3. customcrystals were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customthe obtained oily product was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 1:2)

Sources & evidence

ORD record
ord-2af2835edd13433ab88fad3f2b6631b3
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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