Ethyl bromoacetate → Ethyl 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetate

HRID 1602498Notes

Reaction equation

HRID 1602498 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:42])=[C:18]([CH:41]=2)[NH:19][C:20](=[O:40])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[CH:28][C:29]3[S:30][CH:31]=[C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:33]=3)[CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52]>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:42][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[C:18]([NH:19][C:20](=[O:40])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[CH:28][C:29]4[S:30][CH:31]=[C:32]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[N:33]=4)[CH:22]=3)[CH:41]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 538477505'-[3-(4-Chlorophenylsulfonyl)propyl]-2'-hydroxy-3-[2-(4-phenyl-2-thiazolyl)vinyl]benzanilide

Product 1

HCID 54512577Ethyl 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetateYield 53%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

5'-[3-(4-Chlorophenylsulfonyl)propyl]-2'-hydroxy-3-[2-(4-phenyl-2-thiazolyl)vinyl]benzanilide (0.60 g, 0.98 mmol) was dissolved in dimethylformamide (6 ml), potassium carbonate (0.20 g, 1.45 mmol), a catalytically effective amount of tetrabutylammonium bromide and ethyl bromoacetate (0.13 ml, 1.17 mmol) were added in that order under ice-cooling, followed by 12 hours of stirring at room temperature. Ice-water was added to the reaction solution and the product formed was extracted twice with benzene-ethyl acetate mixed solution (1:1). The resulting organic layer was washed with 5% potassium carbonate aqueous solution and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent=acetone:chloroform=1:100) and crystallized from acetonitrile to give ethyl 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetate (0.36 g, 0.51 mmol, 53%) as colorless crystals.

Workup

  1. temperaturecooling
  2. customthe product formed
  3. extractionwas extracted twice with benzene-ethyl acetate mixed solution (1:1)
  4. washThe resulting organic layer was washed with 5% potassium carbonate aqueous solution and brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent=acetone:chloroform=1:100)
  8. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-9baf7bdf12bc443cb319de1cd75238dd
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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