Ethyl chloroacetate → HCID 58012197, compound

HRID 660873Notes

Reaction equation

HRID 660873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH3:14])[C:11](=[O:15])[NH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:17][C:18]([O:20]CC)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][CH3:14])[C:11](=[O:15])[N:10]([CH2:17][C:18]([OH:20])=[O:19])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 57455731HCID 57455731, compound

Product 1

HCID 58012197HCID 58012197, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

685 mg (3.076 mmol) of 5-(4-chlorophenyl)-1-ethyl-1,3-dihydro-2H-imidazol-2-one from Example 119A are placed in 10 ml acetonitrile, treated with 377 mg (3.076 mmol) of ethyl chloroacetate and 850 mg (6.152 mmol) of potassium carbonate and stirred under reflux overnight. The reaction mixture is evaporated, 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 100:1→50:1) and thus yields 226 mg (26% of theory) of the target compound.

Workup

  1. temperatureunder reflux overnight
  2. customThe reaction mixture is evaporated
  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-13aed2be41ec45a284ebd370c949fb8a
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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