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

HRID 734619Notes

Reaction equation

HRID 734619 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-313ad26ff04d41b9ad75c9179e8dbb24
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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