Phenylacetylene → HCID 23372940, compound

HRID 1899688Notes

Reaction equation

HRID 1899688 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[O:24][N:23]=[C:22]([CH3:25])[C:21]=2[CH3:26])(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(NCC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:7]#[C:8][C:10]2[CH:11]=[CH:12][C:13]([S:16]([NH:19][C:20]3[O:24][N:23]=[C:22]([CH3:25])[C:21]=3[CH3:26])(=[O:17])=[O:18])=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 22616261HCID 22616261, compound

Product 1

HCID 23372940HCID 23372940, compoundYield 163.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8021DiethylamineSolvent

Procedure

To a mixture of phenylacetylene (34.8 ml, 0.32 mmol) and copper(I) iodide (0.25 mg) in diethylamine (2 ml) stirred at room temperature was added 4-iodo-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (1 00 mg, 0.26 mmol) and bis(triphenylphosphine) palladium(II) chloride (1.86 mg). The brown mixture was stirred at room temperature for 4 h. The solvent was removed under reduced pressure and the brownish residue was extracted into 50 ml of ethyl acetate. The organic extract was washed with 1N HCl (2×20 ml) and brine (25 ml). After drying with magnesium sulfate, the solvent was removed to give a brown crystalline solid which was chromatographed on silica gel with 1.5% methanol in chloroform to give 150 mg (81%) brown solid. Recrystallization from ethyl acetate/hexanes gave a white powder, m.p. 198°-200° C. (dec.).

Workup

  1. stirringThe brown mixture was stirred at room temperature for 4 h
  2. customThe solvent was removed under reduced pressure
  3. extractionthe brownish residue was extracted into 50 ml of ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with 1N HCl (2×20 ml) and brine (25 ml)
  6. dry with materialAfter drying with magnesium sulfate
  7. customthe solvent was removed
  8. customto give a brown crystalline solid which
  9. customwas chromatographed on silica gel with 1.5% methanol in chloroform

Sources & evidence

ORD record
ord-d4bbf6fa467f438c993ea77e9b311473
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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