Sulfate Ion → Azulene

HRID 1596808

반응식

HRID 1596808 반응식
[C:1]1(C=O)[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:3](C=O)[CH:2]=1.S([O-])([O-])(=O)=O.Cl.C(NO)(C)(C)C.C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 1117Sulfate IonHCID 516892Sodium BicarbonateHCID 2777896N-tert-butylhydroxylamine hydrochlorideHCID 109761521,3-Azulenedicarboxaldehyde

생성물 1

HCID 9231Azulene수율 225.1%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

반응 조건

온도
95 °C

실험 절차

1,3-Azulenedicarboxaldehyde (600 mg) is dissolved in 6.5 ml of pyridine. Magesium sulfate (1200 mg) and N-tert-butylhydroxylamine hydrochloride (1638 mg) is added to the solution. The mixture is heated with stirring to 95° C. under nitrogen and is stirred for 13 hours. Upon cooling to rt, the reaction mixture is poured into a separator funnel containing 60 ml of CHCl3 and 60 ml of sat aq. NaHCO3. The aqueous layer is separated and washed with three 30 ml portions of CHCl3. The combined organic layers are dried over anhydrous MgSO2, filtered, and evaporated to give the bis-nitrone 34 (940 mg, 89% yield) as dark green crystals. Oxidation potential equals 0.72 V vs SCE. 1H NMR (CDCl3): 10.35 (s, 1 H), 8.65 (d, 2 H, J=10 Hz) 8.11 (s, 2 H), 7.68 (t, 1 H, J=10 Hz), 7.32 (t, 2 H, J=10 Hz), 1.67 (s, 18 H). 13C NMR (CDCl3): 139.9, 135.0, 134.2, 125.8, 125.6, 123.2, 120.5, 69.8. 28.4. IR (thin film): 3052, 2972, 1644, 1564, 1452, 1404, 1356, 1261, 1196, 1124, 1052, and 892 cm−1.

후처리

  1. temperatureThe mixture is heated
  2. stirringis stirred for 13 hours
  3. temperatureUpon cooling to rt
  4. additionthe reaction mixture is poured into a separator funnel
  5. customThe aqueous layer is separated
  6. washwashed with three 30 ml portions of CHCl3
  7. dry with materialThe combined organic layers are dried over anhydrous MgSO2
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-28aa48d792ac4c5c84f95e6fdd06ef71
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291702B1

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