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

HRID 1717689Notes

Reaction equation

HRID 1717689 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-16a1b444a202445f8440d3fcd474aae7
Source dataset
uspto-grants-2010_09
Patent number
US07803956B2

Reaction notes

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