Hydrogen Peroxide → HCID 68902692, compound

HRID 735308Notes

Reaction equation

HRID 735308 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:25]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[C:30]#[N:31])(=[O:27])=[O:26])[CH:19]=[CH:18]2.OO>O.CN(C)C=O>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:25]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[C:30]([NH2:31])=[O:2])(=[O:26])=[O:27])[CH:19]=[CH:18]2

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 68901654HCID 68901654, compound

Product 1

HCID 68902692HCID 68902692, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of potassium carbonate (96 mg, 0.69 mmol) in water (0.5 mL) was added to 2-{[6-(2,4-difluorophenyl)-2-naphthyl]sulfonyl}benzonitrile (Example 2, 138 mg, 0.34 mmol) in N,N-dimethylformamide (6 mL). Hydrogen peroxide (35 wt %, 120 μL, 1.37 mmol) was added dropwise. The reaction was stirred at room temperature overnight. The reaction mixture was diluted with water (60 mL). The resulting precipitate was collected by filtration and recrystallised from ethyl acetate/isohexane to give the title compound (118 mg, 82%). 1H NMR (500 MHz, d6-DMSO) δ 8.68 (1H, s), 8.22 (1H, d, J=8.6 Hz), 8.16 (3H, dd, J=6.9, 15.7 Hz), 8.02 (1H, d, J=8.8 Hz), 7.98 (1H, s), 7.81 (1H, d, J=8.5 Hz), 7.75-7.69 (2H, m), 7.66 (1H, t, J=7.2 Hz), 7.60 (1H, s), 7.47 (1H, d, J=7.2 Hz), 7.45-7.39 (1H, m), 7.27-7.23 (1H, m); m/z (ES+) 407 [(M-NH2)+]

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customrecrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-fe6cfe6f327b40328a4bf2a969883432
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

Loading…