Ethylenediamine → 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole

HRID 254475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254475
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]#[N:11])=[C:4]([CH3:12])[CH:3]=1.[CH2:13](N)[CH2:14][NH2:15].[S]>>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH2:9][C:10]2[NH:15][CH2:14][CH2:13][N:11]=2)=[C:6]([CH3:8])[CH:7]=1

Komponenten

4

Edukt 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 58951703(4-Fluoro-2,6-dimethyl-phenyl)-acetonitrile

Produkt 1

HCID 589518552-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. additionwas poured onto water
  3. extractionextracted with methylene chloride
  4. washthe combined extracts washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient
  9. additioncontaining 1% conc. ammonia

Quellen und Nachweise

ORD-Eintrag
ord-e0abce5e19fb46938388b43c7833f41d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875645B2

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