Sulfuric Acid → 4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-2-pentafluorosulfanylbenzonitrile

HRID 2356662Notes

Reaction equation

HRID 2356662 reaction equation
S(=O)(=O)(O)O.N[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:9][C:8]=1[S:24]([F:29])([F:28])([F:27])([F:26])[F:25].N([O-])=O.[Na+].[Cu][C:35]#[N:36].[C-]#N.[K+]>C(O)(=O)C.O>[O:22]=[C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:23])[N:13]1[C:10]1[CH:11]=[CH:12][C:7]([C:35]#[N:36])=[C:8]([S:24]([F:27])([F:29])([F:26])([F:25])[F:28])[CH:9]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 23668193Sodium NitriteHCID 596421372-(4-Amino-3-pentafluorosulfanylphenyl)isoindole-1,3-dioneHCID 178418546HCID 178418546, compound

Product 1

HCID 596421514-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-2-pentafluorosulfanylbenzonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

0.46 ml (8.24 mmol) of semiconcentrated sulfuric acid was slowly added dropwise at 0° C. to a solution of 1 g (2.74 mmol) of 2-(4-amino-3-pentafluorosulfanylphenyl)isoindole-1,3-dione 51.7 in acetic acid. The mixture was stirred at 0° C. for 10 min; thereafter, a solution of 189.4 mg of sodium nitrite in 2 ml of water was slowly added dropwise with stirring, and the resulting solution was stirred at 0° C. for 30 min. This solution was finally added dropwise to a solution, cooled to 0° C., of 246 mg (2.74 mmol) of copper(I) cyanide and 536 mg (8.23 mmol) of potassium cyanide in 5 ml of water. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for another 3 h. After the reaction had ended, the mixture was added to water and the aqueous phase was extracted by shaking twice with ethyl acetate. The organic phase was dried over magnesium sulfate and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel first with toluene and then with 20/1 toluene/ethyl acetate. 4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-2-pentafluorosulfanylbenzonitrile 51.8 was obtained. 1H NMR: 8.4, m, 2H, 8.1-7.95, m, 5H.

Workup

  1. stirringwith stirring
  2. stirringthe resulting solution was stirred at 0° C. for 30 min
  3. additionThis solution was finally added dropwise to a solution
  4. stirringThe reaction mixture was stirred at 0° C. for 30 min
  5. waitat room temperature for another 3 h
  6. extractionthe aqueous phase was extracted
  7. stirringby shaking twice with ethyl acetate
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated
  11. customthe residue was purified by chromatography on silica gel first with toluene

Sources & evidence

ORD record
ord-d26282adafdd47b3b2921cede389aa7d
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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