Ethyl chloroformate → ethyl 4-iodo-2-methyl-1H-imidazole-1-carboxylate

HRID 422502Notes

Reaction equation

HRID 422502 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH3:7])[NH:5][CH:6]=1.CCN(C(C)C)C(C)C.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1.CN(C1C=CN=CC=1)C>[I:1][C:2]1[N:3]=[C:4]([CH3:7])[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178433060HCID 178433060, compound

Product 1

HCID 66598321ethyl 4-iodo-2-methyl-1H-imidazole-1-carboxylateYield 95.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-iodo-2-methyl-1H-imidazole (162 mg, 0.78 mmol) in THF (2.6 mL, 0.3M) containing DIEA (0.33 mL, 1.95 mmol) and DMAP (47 mg, 0.039 mmol), cooled in a ice bath at 0° C., was added a solution of Ethyl chloroformate (211 mg, 1.95 mmol) in THF (2 mL, 1M). The reaction mixture was heated at 50° C. for 48 h and then concentrated. The residue was dissolved in DCM and the organic layer was washed with saturated NaCl, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (Prepacked column 10 g, DCM/MeOH: 97/3 as eluent) to afford 208 mg of ethyl 4-iodo-2-methyl-1H-imidazole-1-carboxylate (95%) as colorless oil.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 48 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM
  4. washthe organic layer was washed with saturated NaCl
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography (Prepacked column 10 g, DCM/MeOH: 97/3 as eluent)

Sources & evidence

ORD record
ord-cc1cddb27d43467bb0083b1f759e163c
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

Loading…