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

HRID 334793Notes

Reaction equation

HRID 334793 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-ef9b87e74d6d442bba4449959734d202
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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