HCID 58107444, compound → HCID 44235742, compound

HRID 873646Notes

Reaction equation

HRID 873646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:22]([NH2:25])(=[O:24])=[O:23].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:21])[C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[S:22]([NH2:25])(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 58107444HCID 58107444, compoundHCID 131709961Jones' reagent

Product 1

HCID 44235742HCID 44235742, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Chloro-5-{hydroxy-[4-(3-methyl-butoxy)-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 25-75%) followed by recrystallization from ether affording 25 mg of the title compound. 1H NMR (DMSO) 0.93 (s, 3H), 0.95 (s, 3H), 1.64-1.82 (m, 3H), 4.13 (t, 2H, J=6.41 Hz), 7.12 (d, 2H, J=8.67 Hz), 7.75-7.91 (m, 4H), 8.24 (d, 1H, J=1.89). MS (m/z): 380 (M−1). CHN Calc C, 56.62; H, 5.28; N, 3.67. Found C, 56.54; H, 5.04; N, 3.73.

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 25-75%)
  5. customfollowed by recrystallization from ether affording 25 mg of the title compound

Sources & evidence

ORD record
ord-f28030b5b0944c66b3708b7ed512fd27
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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