Ethyl chloroacetate → Ethyl [4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

HRID 660868Notes

Reaction equation

HRID 660868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[NH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][N:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]([CH:13]2[CH2:14][CH2:15]2)[C:11]1=[O:16])[CH3:23]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580118325-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 58011842Ethyl [4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

740 mg (3.15 mmol) of 5-(4-chlorophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one from Example 118A are dissolved in 15 ml acetonitrile and treated with 386 mg (3.15 mmol) of ethyl chloroacetate and 872 mg (6.31 mmol) of potassium carbonate. The mixture is stirred overnight under reflux. It is then concentrated, the residue is partitioned between dichloromethane and water, the organic phase is separated, and this is dried over sodium sulphate and again concentrated. The crude product is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1→100:1) and thus yields 602 mg (57% of theory) of the target compound.

Workup

  1. temperatureunder reflux
  2. concentrationIt is then concentrated
  3. customthe residue is partitioned between dichloromethane and water
  4. customthe organic phase is separated
  5. dry with materialthis is dried over sodium sulphate
  6. concentrationagain concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-4a38b35fe38c4fc69bd7c10fd8be96a0
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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