Benzene → 3-(3-Hydroxyprop-1-ynyl)-N-phenylbenzenesulfonamide

HRID 2217696Notes

Reaction equation

HRID 2217696 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C1C=CC=CC=1.C(N(CC)CC)C.[CH2:31]([OH:34])[C:32]#[CH:33]>Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[OH:34][CH2:31][C:32]#[C:33][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 241BenzeneHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 8190068HCID 8190068, compound

Product 1

HCID 224924823-(3-Hydroxyprop-1-ynyl)-N-phenylbenzenesulfonamideYield 64.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-bromo-N-phenyl-benzenesulfonamide (52a) (1.0 g, 3.2 mmol), benzene (2.4 ml), tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.34 mmol), copper iodide (0.032 g, 0.16 mmol), triethylamine (2.4 ml, 17.2 mmol), and propargyl alcohol (1.0 ml, 17.2 mmol)) was refluxed under argon for 30 min. The reaction mixture was diluted with 5% HCl (50 ml) and product was extracted with ethyl acetate (50 ml). The extract was washed successively with 5% NaHCO3, water and dried (Na2SO4). The solvents were removed under reduced pressure and the product was purified on silica gel with ethyl acetate-hexane (1:1, v/v) as eluent. The title compound (0.59 g, 64%) was obtained as an oil. 1H NMR (DMSO-d6, HMDSO) δ: 4.29 (2H, d, J=6.0 Hz, CH2); 5.36 (1H, t, J=6.0 Hz, OH); 6.94-7.32 (5H, m, C6H5); 7.35-7.91 (4H, m, C6H4); 10.32 (1H, s, NH).

Workup

  1. temperaturewas refluxed under argon for 30 min
  2. extractionwas extracted with ethyl acetate (50 ml)
  3. washThe extract was washed successively with 5% NaHCO3, water
  4. dry with materialdried (Na2SO4)
  5. customThe solvents were removed under reduced pressure
  6. customthe product was purified on silica gel with ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-4cab2c5cd2694b418d17375c1a2aec82
Source dataset
uspto-grants-2008_08
Patent number
US07407988B2

Reaction notes

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