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

HRID 254465Notes

Reaction equation

HRID 254465 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:12][CH3:13].[CH2:15]([NH2:18])[CH2:16][NH2:17]>>[CH2:12]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH3:11])[C:4]=1[CH2:3][C:2]1[NH:17][CH2:16][CH2:15][N:18]=1)[CH3:13]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 589518432-(2,2-Dibromo-vinyl)-1,3-diethyl-benzene

Product 1

HCID 247817142-(2,6-diethyl-benzyl)-4,5-dihydro-1H-imidazole

Procedure

To 20 ml ethylene diamine were added at 0° C. 3.20 g (10 mmol) 2-(2,2-dibromo-vinyl)-1,3-diethyl-benzene and the mixture stirred at ambient temperature for 16 hours. The reaction was quenched by addition of aqueous 2N ammonia, extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. The residue was dissolved in ethyl acetate and crystallization at −10° C. provided 2.85 g 2-(2,6-diethyl-benzyl)-4,5-dihydro-1H-imidazole as colourless solid: MS (ISP): 217.1 ((M+H)+.).

Workup

  1. customThe reaction was quenched by addition of aqueous 2N ammonia
  2. extractionextracted with ethyl acetate
  3. washthe combined extracts washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. customcrystallization at −10° C.

Sources & evidence

ORD record
ord-e6bf00e8904b4827a3d3cb4942afd92b
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

Loading…