Ethylenediamine → 2-(3-bromophenyl)-4,5-dihydro-1H-Imidazole

HRID 29271

Reaktionsgleichung

Reaktionsgleichung von HRID 29271
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[S].[CH2:11](N)[CH2:12][NH2:13]>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:13][CH2:12][CH2:11][N:6]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 3

HCID 3301EthylenediamineHCID 233813-BromobenzonitrileHCID 5362487Sulfur

Produkt 1

HCID 541282862-(3-bromophenyl)-4,5-dihydro-1H-Imidazole

Versuchsvorschrift

To a solution of 3-bromobenzonitrile (500 mg, 2.75 mmol) in ethylenediamine (3.5 mL) was added sulfur (44 mg, 1.4 mmol). The mixture was refluxed overnight then poured onto ice water, which caused the product to precipitate as a white solid. The product was isolated by vacuum filtration and dried in a vacuum oven (545 mg, 88%). 1H-NMR (CDCl3) δ 7.93 (t, J=1.7 Hz, 1H), 7.68 (ddd, J=7.8, 1.2, 1.2 Hz, 1H), 7.56 (dddd, J=7.8, 0.9, 0.9, 0.9 Hz, 1H), 7.26 (dd, J=10.5, 8.0 Hz, 1H), 3.78 (br s, 4H).

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. additionthen poured onto ice water, which
  3. customto precipitate as a white solid
  4. customThe product was isolated by vacuum filtration
  5. customdried in a vacuum oven (545 mg, 88%)

Quellen und Nachweise

ORD-Eintrag
ord-396e1a9866ed4c4b8c9948fd1834b2a0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420066B2

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