Sulfate Ion → Azulene

HRID 1596808ノート

反応式

HRID 1596808 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 9231Azulene収率 225.1%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

反応条件

温度
95 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28aa48d792ac4c5c84f95e6fdd06ef71
出典データセット
uspto-grants-2001_09
特許番号
US06291702B1

反応ノート

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