Hydrogen Peroxide → 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-2,4-dioxo-1-imidazolidinyl]-2-fluorobenzamide

HRID 570770Notes

Reaction equation

HRID 570770 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[N:11]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[C:19]([F:26])[CH:18]=3)[C:10]2=S)=[CH:5][C:4]=1[C:28]([F:31])([F:30])[F:29])#[N:2].[OH:32]O>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[N:11]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[C:19]([F:26])[CH:18]=3)[C:10]2=[O:32])=[CH:5][C:4]=1[C:28]([F:31])([F:30])[F:29])#[N:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 70678916N-Desmethylenzalutamide

Product 1

HCID 468985234-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-2,4-dioxo-1-imidazolidinyl]-2-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluorobenzamide (Compound (MII)) (1.48 g, 3.4 mmol) in ethanol (60 mL) was added 30% aqueous H2O2 (30 mL) at room temperature. The solution was heated to reflux for 1 h. After removal of ethanol, brine (100 mL) was added and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product that was purified by silica gel chromatography. MS (m/z): 435 (M+1). HPLC: Column, YMC ODS A, 4.6×150 mm, 5 μm, Mobile Phase A: 10 mM Ammonium acetate, Mobile Phase B: Acetonitrile, Gradient, 10% B up to 2 min, 10% to 90% B in 6 min, hold for 10 min, 90% to 10% B in 4 min, Retention time, 9.548 min, HPLC Purity, 98.08%, Flow Rate, 1 mL/min. 1H NMR (CDCl3, Freebase): δ (ppm) 8.3 (t, 1H), 8.18 (s, 1H), 8.2 (d, 1H), 7.96 (d, 1H), 7.25 (m, 2H), 6.65 (bd, 1H), 5.9 (bs, 1H) 1.65 (s, 6H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. customAfter removal of ethanol, brine (100 mL)
  4. additionwas added
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab1b5fab25bb4b3eb93cb4af9df52c67
Source dataset
uspto-grants-2015_05
Patent number
US09023879B2

Reaction notes

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