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

HRID 660870Notes

Reaction equation

HRID 660870 reaction equation
[Br: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]([Br: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 574557335-(4-bromophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 58012242Ethyl [4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

392 mg (1.40 mmol) of 5-(4-bromophenyl)-1-cyclopropyl-1,3-dihydro-2H-imidazol-2-one from Example 120A are dissolved in 7.7 ml acetonitrile, treated with 172 mg (1.40 mmol) of ethyl chloroacetate and 388 mg (2.81 mmol) of potassium carbonate and heated under reflux for two hours. After cooling, this is filtered, the filtrate evaporated, and the residue partitioned between ethyl acetate and water, the organic phase is separated, dried over sodium sulphate and again concentrated. 502 mg (98% of theory) of the target compound, which is reacted without further purification, are thus obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for two hours
  3. temperatureAfter cooling
  4. filtrationthis is filtered
  5. customthe filtrate evaporated
  6. customthe residue partitioned between ethyl acetate and water
  7. customthe organic phase is separated
  8. dry with materialdried over sodium sulphate
  9. concentrationagain concentrated
  10. custom502 mg (98% of theory) of the target compound, which is reacted without further purification
  11. customare thus obtained

Sources & evidence

ORD record
ord-2b949631f1144e4081fce5fccb51ea91
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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