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

HRID 2180430Notes

Reaction equation

HRID 2180430 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-f74ff3c0820e454da2a8f59171c3d5b0
Source dataset
uspto-grants-2005_05
Patent number
US06888027B2

Reaction notes

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