Ethylenediamine → 2-[(4,5-Dihydro-1H-imidazol-2-yl)phenylmethyl]pyridine

HRID 1679773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679773
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:14]#[N:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:16](N)[CH2:17][NH2:18].[S]>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:14]1[NH:18][CH2:17][CH2:16][N:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 3

HCID 3301EthylenediamineHCID 95510alpha-Phenyl-2-pyridineacetonitrileHCID 5362487Sulfur

Produkt 1

HCID 537623412-[(4,5-Dihydro-1H-imidazol-2-yl)phenylmethyl]pyridine

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

Under a nitrogen atmosphere, carefully reflux (bath temperature of 125° C) a mixture containing 19.4 g. of 2-pyridylbenzyl cyanide, 6.6 g. of ethylene diamine and 0.2 g. of sulphur for 5 hrs. Cool the reaction mixture and under a nitrogen atmosphere dissolve the residue in 300 ml. of benzene, and water wash, dry (over anhydrous potassium carbonate) and filter the benzene solution. Concentrate the filtrate to a small volume whereupon the product crystallizes. Filter the crystals to yield 2-[α-(2-pyridyl) benzyl]-imidazoline, m.p. 134°-136° C. The maleate salt, m.p. 132°-135° C, is prepared from maleic acid and is crystallized from isopropanol.

Aufarbeitung

  1. additioncontaining 19.4 g
  2. temperatureCool the reaction mixture
  3. dissolutionunder a nitrogen atmosphere dissolve the residue in 300 ml
  4. washof benzene, and water wash
  5. dry with materialdry (over anhydrous potassium carbonate)
  6. filtrationfilter the benzene solution
  7. concentrationConcentrate the filtrate to a small volume whereupon the product
  8. customcrystallizes
  9. filtrationFilter the crystals

Quellen und Nachweise

ORD-Eintrag
ord-e531cf7672364b8eb0a2f85db94a49e0
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04081544

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