Iodine → Ammonia

HRID 46162

Reaktionsgleichung

Reaktionsgleichung von HRID 46162
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH2:11]([NH2:14])[CH2:12][NH2:13].C([O-])([O-])=O.[K+].[K+].II>CC(O)(C)C.[O-]S([O-])=O.[Na+].[Na+]>[NH3:13].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[NH:13][CH2:12][CH2:11][N:14]=2)[CH:8]=[CH:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 807IodineHCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 115693-Methoxybenzaldehyde

Produkt 2

HCID 222AmmoniaHCID 37712312-(3-methoxyphenyl)-4,5-dihydro-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6386tert-ButanolLösungsmittelHCID 24437Sodium SulfiteLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 3-methoxybenzaldehyde (0.895 ml) in t-BuOH (30 ml) was added ethylenediamine (0.546 ml) at room temperature. After 30 min K2CO3 (3.05 g) and I2 (2.330 g) were added then the mixture was heated to 70° C. After 4 h the mixture was diluted with saturated aqueous Na2SO3 and extracted with CHCl3 (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated. Flash column chromatography (gradient, 0-10% MeOH/CHCl3 saturated with NH3) gave 2-(3-methoxyphenyl)-4,5-dihydro-1H-imidazole as a pale yellow oil which solidified under vacuum (1.05 g): 1H-NMR (500 MHz, CDCl3) δ 7.38 (m, 2 H), 7.32 (t, J=8.3 Hz, 1 H), 7.01 (m, 1 H), 6.90 (br, 1 H), 3.78 (s, 3 H), 3.59 (br, 2 H), 2.50 (t, J=1.71 Hz, 2 H).

Aufarbeitung

  1. extractionextracted with CHCl3 (3×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-34a3447556524d6faae8f69d7a2c8012
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541595B2

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