Water → HCID 22916333, compound

HRID 1023854Notes

Reaction equation

HRID 1023854 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178418822HCID 178418822, compound

Product 1

HCID 22916333HCID 22916333, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-phenyl imidazole (245.1 mg, 1.7 mmol,), Et3N (258.0 mg, 2.6 mmol), and DMAP (20.1 mg, 170.0 μmol) in DCM (5 mL) was slowly added ethyl chloroformate (276.7 mg, 2.6 mmol) at room temperature. The reaction was allowed to stir overnight at room temperature. The solution was poured into water and the organic layer was washed with water, brine and dried (Na2SO4). The crude residue was purified by column chromatography (30% EtOAc/hexanes) to afford a colorless solid (301.0 mg, 80% yield). 1H NMR: 1.47 (t, 3H, J=6.9 Hz), 4.50 (q, 2H, J=7.0 Hz), 7.30 (t, 1H, J=7.0 Hz), 7.41 (t, 2H, J=7.5 Hz), 7.69 (s, 1H), 7.80 (d, 2H, J=7.9 Hz), 8.2 (s, 1H)

Workup

  1. customat room temperature
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customThe crude residue was purified by column chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dc0936629c414fb59e59bdda9d3e20eb
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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