Water → HCID 11232442, compound

HRID 1590620Notes

Reaction equation

HRID 1590620 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O.[Cu]I>[C:24]1([C:30]#[C:31][C:2]2[N:7]=[N:6][C:5]([S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 19009006HCID 19009006, compound

Product 1

HCID 11232442HCID 11232442, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-chloro-3-phenylsulfonylpyridazine (8.4 g) bis(triphenylphosphine)palladium(II) chloride (98%; 0.24 g), copper(I) iodide (95%; 63 mg), and triethylamine (9.2 ml) in N,N-dimethylformamide (84 ml) was added phenylacetylene (4.7 ml), and the mixture was stirred for 0.5 hour at 80° C. After being cooled to room temperature, water (168 ml) was added to the reaction mixture. The precipitate formed was collected, washed with water, and dried. Recrystallization of the crude product from a mixture of diisopropyl ether and acetone (2:1) gave 6-(2-phenylethynyl)-3-phenylsulfonylpyridazine (5.5 g). After the mother liquor was concentrated in vacuo, the residue was triturated with acetone. The precipitate was collected and dried to give a second crop of the pure material (2.0 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with water
  5. customdried
  6. customRecrystallization of the crude product
  7. additionfrom a mixture of diisopropyl ether and acetone (2:1)

Sources & evidence

ORD record
ord-41cff87a10c04e47a151e1dd5a5c729b
Source dataset
uspto-grants-1993_04
Patent number
US05204346

Reaction notes

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