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

HRID 2250850Notes

Reaction equation

HRID 2250850 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 (prepared in example 5) in acetic acid. The mixture was stirred at 0° C. for 10 min; then 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 afterward at room temperature for another 3 h. After the end of the reaction, the mixture was added to water and the aqueous phase extracted twice with ethyl acetate. The organic phase was dried over magnesium sulfate and filtered, the filtrate was concentrated and the residue purified chromatographically 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 was obtained. 1H NMR (500 MHz; d6-dmso: δ [ppm]=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 and afterward at room temperature for another 3 h
  5. customAfter the end of the reaction
  6. extractionthe aqueous phase extracted twice with ethyl acetate
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customthe residue purified chromatographically on silica gel first with toluene

Sources & evidence

ORD record
ord-a4c2830e098441f8b007f7ecf2a74893
Source dataset
uspto-grants-2008_01
Patent number
US07317124B2

Reaction notes

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