Benzoyl Peroxide → HCID 10115151, compound

HRID 276192Notes

Reaction equation

HRID 276192 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)/[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:26]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:26][C:13]1[S:12][C:11]([NH:10][C:8](=[O:9])/[C:7](/[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6]/[CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 46946861HCID 46946861, compound

Product 1

HCID 10115151HCID 10115151, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of (E)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-acrylamide (prepared in Example 3, 0.44 g, 1.17 mmol) and N-bromosuccinimide (0.20 g, 1.17 mmol) in carbon tetrachloride (4 mL) at 25° C. was treated with benzoyl peroxide (14.17 mg, 0.058 mmol). The resulting reaction mixture was heated to 90° C. where it was stirred overnight at this temperature. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL). The organic phase was then washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 to 1/1 hexanes/ethyl acetate) afforded (E)-N-(5-bromo-thiazol-2-yl)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-acrylamide (115 mg, 22%) as white solid: mp 202-205° C.

Workup

  1. customThe resulting reaction mixture
  2. temperatureto cool to 25° C.
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washThe organic phase was then washed with water (1×50 mL)
  6. dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e3539e73b774271abd217a2e0455c34
Source dataset
uspto-grants-2002_03
Patent number
US06353111B1

Reaction notes

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