HCID 58107422, compound → HCID 44235744, compound

HRID 873650Notes

Reaction equation

HRID 873650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)[OH:9])=[CH:4][C:3]=1[S:23]([NH2:26])(=[O:25])=[O:24].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:9])[C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:15]=2)=[CH:4][C:3]=1[S:23]([NH2:26])(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 58107422HCID 58107422, compoundHCID 131709961Jones' reagent

Product 1

HCID 44235744HCID 44235744, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Chloro-5-[(4-hexyloxy-phenyl)-hydroxy-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 30 mg of the title compound. 1H NMR (DMSO) 0.88 (t, 3H, J=6.78 Hz), 1.28-1.45 (m, 6H), 1.70-1.79 (m, 2H), 4.09 (t, 2H, J=6.4 Hz), 7.10 (d, 2H, J=9.04 Hz), 7.75-7.90 (m, 4H), 8.24 (d, 1H, J=1.89). MS (m/z): 396 (M+1).

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 30 mg of the title compound

Sources & evidence

ORD record
ord-52ce6611b837427e8e14ddd3fd5706f0
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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