Allyl Alcohol → N-[3-(3-Oxo-propyl)-phenyl]-methanesulfonamide

HRID 2373671Notes

Reaction equation

HRID 2373671 reaction equation
I[C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:13]([OH:16])[CH:14]=[CH2:15].C(=O)([O-])O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.Cl.[Pd](Cl)Cl>[O:16]=[CH:13][CH2:14][CH2:15][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 21830928N-(3-iodophenyl)methanesulfonamide

Product 1

HCID 57444373N-[3-(3-Oxo-propyl)-phenyl]-methanesulfonamideYield 60.5%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3-iodo-phenyl)-methanesulfonamide (2.4 g, 8 mmol), tetra-n-butyl-ammonium chloride (2.22 g, 8 mmol), allyl alcohol (0.7 g, 12 mmol), sodium hydrogencarbonate (1.6 g, 19 mmol) and palladium(II)chloride (0.36 g, 1.8 mmol) in anhydrous dimethylformamide (30 mL) was stirred at room temperature for 48 h under argon. The mixture was then diluted with 5% aqueous hydrochloric acid (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were dried (sodium sulfate) and evaporated in vacuo. The crude product was purified by silica gel chromatography (ethyl acetate in hexane, 30% to 50%) to give the title compound as an amber oil (1.1 g, 60%).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. customevaporated in vacuo
  4. customThe crude product was purified by silica gel chromatography (ethyl acetate in hexane, 30% to 50%)

Sources & evidence

ORD record
ord-4b69b5898ae34b7fb755a55d87061940
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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