Ethyl chloroacetate → Ethyl [4-(5-chloro-2-thienyl)-3-(2-fluorobenzyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

HRID 660909Notes

Reaction equation

HRID 660909 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10](=[O:20])[NH:9][CH:8]=2)=[CH:4][CH:3]=1.Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:9]1[CH:8]=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]1=[O:20])[CH3:27]

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580122955-(5-chloro-2-thienyl)-1-(2-fluorobenzyl)-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 58012258Ethyl [4-(5-chloro-2-thienyl)-3-(2-fluorobenzyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

650 mg (2.15 mmol) of 5-(5-chloro-2-thienyl)-1-(2-fluorobenzyl)-1,3-dihydro-2H-imidazol-2-one from Example 236A, 516 mg (4.21 mmol) of ethyl chloroacetate and 582 mg (4.21 mmol) of potassium carbonate are stirred in 12 ml acetonitrile for 7 hrs at 80° C. The reaction solution is diluted with ethyl acetate and washed three times with saturated sodium chloride solution. The organic phase is dried over sodium sulphate. After filtration from the drying agent, the filtrate is concentrated in vacuo. After purification by flash chromatography over silica gel (eluent: cyclohexane/ethyl acetate first 5:1, then 1:1), 610 mg (74% of theory) of the target compound are obtained.

Workup

  1. washwashed three times with saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationAfter filtration from the drying agent
  4. concentrationthe filtrate is concentrated in vacuo
  5. customAfter purification by flash chromatography over silica gel (eluent
  6. customcyclohexane/ethyl acetate first 5:1, then 1:1), 610 mg (74% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-f0c2124665ae45cc9ce4b67f4bccbb7a
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

Loading…