HCID 58107396, compound → HCID 44235743, compound

HRID 1810177Notes

Reaction equation

HRID 1810177 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][CH3:21])=[CH:12][CH:11]=2)[OH:9])=[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:9])[C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][CH:15]=2)=[CH:4][C:3]=1[S:22]([NH2:25])(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 58107396HCID 58107396, compoundHCID 131709961Jones' reagent

Product 1

HCID 44235743HCID 44235743, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Chloro-5-[(4-pentyloxy-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 15 mg of the title compound. 1H NMR (DMSO) 0.90 (t, 3H, J=6.79 Hz), 1.31-1.46 (m, 4H), 1.70-1.79 (m, 2H), 4.09 (t, 2H, J=6.49 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): 382 (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 15 mg of the title compound

Sources & evidence

ORD record
ord-d6c4cec9c47f4210856e41df6af88aa9
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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