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

HRID 2080933노트

반응식

HRID 2080933 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매3회

반응 조건

온도
0 °C

실험 절차

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/l 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).

후처리

  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

출처 및 근거

ORD 기록
ord-aa2789ce19d542a6a92ba339e2ab20a4
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932416B2

반응 노트

불러오는 중…