Hydrochloric Acid → HCID 19423414, compound

HRID 743030Notes

Reaction equation

HRID 743030 reaction equation
I[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:19]([C:21]1[CH:22]=[CH:23][C:24]([OH:32])=[C:25]([CH:31]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])#[CH:20].C(N(CC)CC)C.Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCCC1>[OH:32][C:24]1[CH:23]=[CH:22][C:21]([C:19]#[C:20][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])[CH:3]=2)=[CH:31][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 19423366Ethyl 5-ethynyl-2-hydroxybenzoateHCID 194233943-Iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide

Product 1

HCID 19423414HCID 19423414, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide (18.7 g, 50 mmol), ethyl 5-ethynyl-2-hydroxybenzoate (9.5 g, 50 mmol), triethylamine (65 ml) and tetrahydrofuran (65 ml) were stirred at 60° C. Dichlorobis(triphenylphosphine)palladium (250 mg, 0.36 mmol) and copper(1)iodide (140 mg, 0.7 mmol) were added with stirring. After 1 h the solution was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried, treated with activated carbon and the solvent evaporated. The residue was recrystallized from methanol, then from toluene and finally from acetic acid. Yield 12.7 g 58%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. additiontreated with activated carbon
  5. customthe solvent evaporated
  6. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e0b83b07f8724a92a0c3fbe562ddb6c4
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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