Benzene → HCID 22492482, compound

HRID 226173Notes

Reaction equation

HRID 226173 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 22492482HCID 22492482, compoundYield 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-68aa67cddc2b4861876da55b2fec1880
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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