Potassium Cyanide → HCID 15434618, compound

HRID 1858005Notes

Reaction equation

HRID 1858005 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[C:17](OS(C(F)(F)F)(=O)=O)=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.[C-:32]#[N:33].[K+]>O1CCOCC1.[Cl-].[Na+].O.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>[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[C:17]([C:32]#[N:33])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([NH2:29])(=[O:27])=[O:28])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 22125701HCID 22125701, compound

Product 1

HCID 15434618HCID 15434618, compoundYield 59.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethyl-sulfonyloxy-2-naphthalenesulfonamide (1.0 g, 2.1 mmol) [pre pared as described in step 2 above], potassium cyanide (0.15 mg, 2.3 mmol), and tetrakis(triphenylphosphine)palladium(0) in dioxane (15 ml) was heated at reflux under argon. After 2 h, the reaction mixture was cooled to RT, poured into brine, and the product was extracted into ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution, 20-50% ethyl acetate/hexane) and then recrystallized from ethyl acetate-hexane to give 0.44 g of 5-(4-fluorobenzoyl)-6-cyano-2-naphthalenesulfonamide as a white solid (54% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon
  3. extractionthe product was extracted into ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (gradient elution, 20-50% ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d72d649b75454b248c92aa4576aed0a2
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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