Water → HCID 22137375, compound

HRID 1827568Notes

Reaction equation

HRID 1827568 reaction equation
[OH:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([C:17]2[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=2)[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:26]([OH:29])[CH:27]=[CH2:28].C(=O)(O)[O-].[Na+].O>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C>[OH:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([C:17]2[CH:22]=[CH:21][C:20]([CH2:28][CH2:27][CH:26]=[O:29])=[CH:19][CH:18]=2)[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 22137317HCID 22137317, compound

Product 1

HCID 22137375HCID 22137375, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(4-hydroxy-benzyl)-N-(4-iodo-phenyl)-benzenesulfonamide (3.20 g, 6.88 mmol) in 16 mL dimethylformamide was added allyl alcohol (1.20 mL, 17.60 mmol), Pd(OAc)2 (0.094 g, 0.42 mmol), sodium bicarbonate (1.42 g, 16.9 mmol), and tetrabutylammonium chloride (1.95 g, 7.02 mmol). The reaction was stirred at 50° C. for 19 hr. The reaction mixture was cooled, water and ethyl acetate were added, and the mixture was filtered through diatomaceous earth. The aqueous layer was washed twice with ethyl acetate. The combined organic layers were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (25% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2.12 g (78%) of N-(4-hydroxy-benzyl)-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. washThe aqueous layer was washed twice with ethyl acetate
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14c2f7154d404b7a9d2d4f1e16dfa54c
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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