18-Crown-6 → HCID 19437132, compound

HRID 1735387Notes

Reaction equation

HRID 1735387 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.BrN1C(=O)CCC1=O.[C:18]([O-:21])(=[O:20])[CH3:19].[K+].C1OCCOCCOCCOCCOCCOC1>C(Cl)(Cl)(Cl)Cl.C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:21][C:18](=[O:20])[CH3:19])[C:5]([Br:9])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 2855718-Crown-6HCID 67184N-bromobutanimideHCID 517044Potassium AcetateHCID 27344292,5-Dibromo-4-methylpyridine

Product 1

HCID 19437132HCID 19437132, compoundYield 20.5%

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

2.5-Dibromo-4-methylpyridine(26.06 g, 103.8 mmol) and N-bromosuccinimide (27.72 g, 155.7 mmol) in carbon tetrachloride (500 ml) were heated to reflux over a 150 W light bulb for 2 h. Cooling to 5° C., filtration and evaporation to dryness under reduced pressure gave the crude brominated products which were treated with potassium acetate (66.0 g, 673 mmol) and 18-crown-6 (3.00 g, 11.4 mmol) in acetonitrile (500 ml) at room temperature for 40 h. Filtration and evaporation of the filtrate to dryness gave the crude products which were dissolved in ethyl acetate, washed with saturated aqueous potassium bromide solution, the organic phase dried (Na2SO4) and evaporated to dryness under reduced pressure with purification by flash chromatography using hexane/ethyl acetate (6:1) as eluent giving the title compound (6.56 g. 19%) as a white solid: δH (CDCl3), 2.22 (3H, s, CH3), 5.12 (2H, s, CH2OAc), 17.50 (1H, s, 3-H), 18.45 (1H, s, 6-H); m/z (E.I.) 308 (MH+, 3%), 230 (100%): (Found: M+, 307.8926. C8H8NO2Br requires M. 307.89221.

Workup

  1. temperatureto reflux over a 150 W light bulb for 2 h
  2. filtrationfiltration and evaporation to dryness under reduced pressure
  3. customgave the crude brominated products which
  4. filtrationFiltration and evaporation of the filtrate to dryness
  5. customgave the crude products which
  6. washwashed with saturated aqueous potassium bromide solution
  7. dry with materialthe organic phase dried (Na2SO4)
  8. customevaporated to dryness under reduced pressure with purification by flash chromatography

Sources & evidence

ORD record
ord-f2c6761ef7ab446fa9dbfcab36bdf12c
Source dataset
uspto-grants-1996_07
Patent number
US05536745

Reaction notes

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