Acetic Acid → HCID 178423882, compound

HRID 1429112Notes

Reaction equation

HRID 1429112 reaction equation
[I:1][C:2]1[N:3](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:4]=[C:5]([C:7]2[S:8][C:9]([CH3:12])=[CH:10][CH:11]=2)[N:6]=1.CC(O)=O>CO.C1(C)C=CC=CC=1>[I:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]2[S:8][C:9]([CH3:12])=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 675120362-Iodo-4-(5-methylthiophen-2-yl)-1-trityl-1H-imidazole

Product 1

HCID 178423882HCID 178423882, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-iodo-4-(5-methylthiophen-2-yl)-1-trityl-1H-imidazole 2 (2.57 g, 4.83 mmol) and AcOH (3 mL) in MeOH (120 mL) was heated under reflux (2 h). The mixture was allowed to cool to room temperature and then concentrated to give a residue. The residue was taken up in toluene and concentrated to five a residue. The residue was diluted with CH2Cl2, H2O, saturated aqueous NaHCO3 and the organic phase was separated. The aqueous phase was re-extracted (CH2Cl2) and the combined organics were washed (saturated aqueous NaCl), dried (MgSO4), filtered and concentrated to give a residue. The residue was purified by flash chromatography (EtOAc/hexanes 15:85 then 30:70 then 40:60) to give 2-iodo-4-(5-methylthiophen-2-yl)-1H-imidazole 3 (1.2 g, 86%) as a colourless solid. 1H NMR (CDCl3, 400 MHz) □ 2.48 (d, J=1.0 Hz, 3H), 6.65-6.68 (m, 1H), 7.03 (d, J=3.5 Hz 1H), 7.14 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux (2 h)
  3. concentrationconcentrated
  4. customto give a residue
  5. concentrationconcentrated to five a residue
  6. additionThe residue was diluted with CH2Cl2, H2O, saturated aqueous NaHCO3
  7. customthe organic phase was separated
  8. extractionThe aqueous phase was re-extracted (CH2Cl2)
  9. washthe combined organics were washed (saturated aqueous NaCl)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give a residue
  14. customThe residue was purified by flash chromatography (EtOAc/hexanes 15:85

Sources & evidence

ORD record
ord-1e6d4deefa274024a1a7b72524dac9d6
Source dataset
uspto-grants-2015_01
Patent number
US08937303B2

Reaction notes

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