4,5-dihydro-1H-imidazole-2-sulfonic acid → N-(imidazolidin-2-ylidene)-1-phenyl-2-(pyridin-4-yl)ethanamine

HRID 1027692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1027692
[C:1]1([CH:7]([NH2:15])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:16]1[CH2:20][CH2:19][N:18]=[C:17]1S(O)(=O)=O>CC(O)CC.O>[NH:16]1[CH2:20][CH2:19][NH:18][C:17]1=[N:15][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acidHCID 104653421-Phenyl-2-(pyridin-4-yl)ethanamine

Produkt 1

HCID 178420220N-(imidazolidin-2-ylidene)-1-phenyl-2-(pyridin-4-yl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6568(+-)-2-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 1-phenyl-2-(pyridin-4-yl)ethanamine (0.23 g, 1.18 mmol), and 4,5-dihydro-1H-imidazole-2-sulfonic acid (0.18 g, 1.16 mmol) in 2-butanol (5 mL), water (1 mL) were heated at 110° C. for 3 hours. The solution was cooled to room temperature. The solvents were removed under vacuum. The residue was dissolved in methanol, and added amino modified silica gel. The solvent was removed under vacuum. Purification by chromatography on amino modified silica gel (100% ethyl acetate to 7% methanol in dichloromethane) gave N-(imidazolidin-2-ylidene)-1-phenyl-2-(pyridin-4-yl)ethanamine Compound 3 as a while solid (0.21 g, 0.80 mmol, 67% yield).

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. customThe solvents were removed under vacuum
  3. dissolutionThe residue was dissolved in methanol
  4. additionadded amino
  5. customThe solvent was removed under vacuum
  6. customPurification by chromatography on amino

Quellen und Nachweise

ORD-Eintrag
ord-bcd1a1d75761465f8c0a6f47c568df0d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735399B2

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