Iodine → 2-(4-(methylthio)phenyl)-4,5-dihydro-1H-imidazole

HRID 44815Notes

Reaction equation

HRID 44815 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13].C([O-])([O-])=O.[K+].[K+].II>CC(O)(C)C>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]2[NH:13][CH2:12][CH2:11][N:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 807IodineHCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 442691062-(4-(methylthio)phenyl)-4,5-dihydro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-(methylthio)benzaldehyde (1-Im-1, 10 g, 1.0 eq) in 1000 mL of t-BuOH, ethylene diamine (1.1 eq) was added. The mixture was stirred at rt under Ar for 30 min, then K2CO3 (3.0 eq) and I2 (1.25 eq) were added to the mixture. This mixture was stirred at 70° C. for 3 h, then was quenched with aqueous Na2SO3 until the color of iodine disappeared, then extracted with CHCl3. The organic layer was washed with NaHCO3 and brine and dried with Na2SO4. The solvent was removed to give 2-(4-(methylthio)phenyl)-4,5-dihydro-1H-imidazole (compound 2-Im-1).

Workup

  1. stirringThis mixture was stirred at 70° C. for 3 h
  2. customwas quenched with aqueous Na2SO3 until the color of iodine
  3. extractionextracted with CHCl3
  4. washThe organic layer was washed with NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-89925d3142eb454da02e97f232fbdfa9
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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