Ethylenediamine → 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole

HRID 254475Notes

Reaction equation

HRID 254475 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]#[N:11])=[C:4]([CH3:12])[CH:3]=1.[CH2:13](N)[CH2:14][NH2:15].[S]>>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH2:9][C:10]2[NH:15][CH2:14][CH2:13][N:11]=2)=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 58951703(4-Fluoro-2,6-dimethyl-phenyl)-acetonitrile

Product 1

HCID 589518552-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole

Conditions

Temperature
200 °C

Procedure

A mixture of 1.30 g (8 mmol) (4-fluoro-2,6-dimethyl-phenyl)-acetonitrile, 3.83 g (4.27 ml, 64 mmol) ethylene diamine and 0.128 g (4 mmol) sulfur in a pressurized glass tube was heated under microwave irradiation to 200° C. for 20 min. The cooled reaction mixture was poured onto water, extracted with methylene chloride, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient containing 1% conc. ammonia provided 2-(4-fluoro-2,6-dimethyl-benzyl)-4,5-dihydro-1H-imidazole as light yellow solid: MS (EI): 206.1 ((M+.), 100%).

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured onto water
  3. extractionextracted with methylene chloride
  4. washthe combined extracts washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash-chromatography over silica gel with a ethyl acetate/methanol gradient
  9. additioncontaining 1% conc. ammonia

Sources & evidence

ORD record
ord-e0abce5e19fb46938388b43c7833f41d
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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