HCID 58107491, compound → HCID 58107484, compound

HRID 873651Notes

Reaction equation

HRID 873651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:21]([NH2:24])(=[O:23])=[O:22].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:18])([F:17])[F:19])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:21]([NH2:24])(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 58107491HCID 58107491, compoundHCID 131709961Jones' reagent

Product 1

HCID 58107484HCID 58107484, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Chloro-5-[hydroxy-(4-trifluoromethoxy-phenyl)-methyl]-benzenesulfonamide is dissolved in acetone (10 mL), and treated with a solution of Jones reagent (3 M in water, 0.91 mmol). The reaction is allowed to stir for 30 minutes. The reaction is diluted with water and extracted with dichloromethane. The organic phase is separated and concentrated in vacuo. The residue is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-50%) affording 92 mg of the title compound. 1H NMR (CDCl3) 5.20 (s, 2H), 7.35 (d, 2H, J=8.3 Hz), 7.70 (d, 1H, J=8.3), 7.84 (d, 2H, J=8.7 Hz), 7.95 (dd, 1 h, J=1.9, 8.3), 8.48 (d, 1H, J=1.9). MS (m/z): 378 (M−1). CHN Calc C, 44.28; H, 2.39; N, 3.69. Found C, 43.97; H, 2.22; N, 3.60.

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase is separated
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-50%)

Sources & evidence

ORD record
ord-6d1b84b9f1b248e19fd1ea9b6c020f0e
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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