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

HRID 1443375Notes

Reaction equation

HRID 1443375 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-4fce2279ce60496eb3297c57714317a3
Source dataset
uspto-grants-2010_02
Patent number
US07659412B2

Reaction notes

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