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

HRID 29271

Reaction equation

HRID 29271 reaction equation
[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

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 233813-BromobenzonitrileHCID 5362487Sulfur

Product 1

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

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-396e1a9866ed4c4b8c9948fd1834b2a0
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Linked notes

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