Benzoyl Peroxide → (E)-N-(5-bromo-thiazol-2-yl)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylamide

HRID 276215Notes

Reaction equation

HRID 276215 reaction equation
[CH:1]1(/[CH:8]=[C:9](\[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)/[C:10]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:28]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:28][C:15]1[S:14][C:13]([NH:12][C:10](=[O:11])/[C:9](/[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:8]/[CH:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10111868(E)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-acrylamide

Product 1

HCID 10299638(E)-N-(5-bromo-thiazol-2-yl)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylamideYield 36%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of (E)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-acrylamide (prepared in Example 5, 202 mg, 0.5 mmol) and N-bromosuccinimide (89 mg, 0.5 mmol) in carbon tetrachloride (2 mL) at 25° C. was treated with benzoyl peroxide (6 mg, 0.025 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 (25 mL). The organic phase was then washed with water (1×30 mL) and a saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded the (E)-N-(5-bromo-thiazol-2-yl)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylamide (86 mg, 36%) as a white solid: mp 159-163° 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 (25 mL)
  5. washThe organic phase was then washed with water (1×30 mL)
  6. dry with materiala saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a9617aa6fa64e8abc4a091d0df0bdce
Source dataset
uspto-grants-2002_03
Patent number
US06353111B1

Reaction notes

Loading…