Anthranilic Acid → 1,3-Dithiaindane, 2-(3-methylbutyl)oxy-

HRID 483959

Reaktionsgleichung

Reaktionsgleichung von HRID 483959
[CH2:1]([OH:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[C:7](=[S:9])=[S:8].C(O)(=O)[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)N>ClCCCl.O1CCOCC1>[CH2:1]([O:6][CH:7]1[S:9][C:17]2[CH:16]=[CH:15][CH:14]=[CH:12][C:11]=2[S:8]1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Komponenten

6

Edukt 3

HCID 227Anthranilic AcidHCID 6348Carbon DisulfideHCID 31260Isoamyl Alcohol

Produkt 1

HCID 5926411,3-Dithiaindane, 2-(3-methylbutyl)oxy-Ausbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

42.1 g (0.36 mole) of isoamyl nitrile, 52.8 g (0.60 mole) of isoamyl alcohol and 150 ml of carbon disulfide were dissolved in 800 ml of 1,2-dichloroethane. The reaction solution was mildly heated under reflux at a temperature of about 80° C. A solution of 41.1 g (0.30 mole) of anthranilic acid in 100 ml of dioxane was added dropwise to the reaction solution over 1.5 hours. The reaction solution was further heated under reflux for an additional 30 minutes. The resulting mixture was washed successively with water, a saturated aqueous solution of sodium carbonate and water, and then dried over magnesium sulfate. The resulting organic solution was concentrated under reduced pressure. The residue was then purified through silica gel column chromatography (75 to 230 mesh; eluent: benzene) to obtain 28.8 g (yield: 40%) of the desired compound (V) as a pale yellow oil. The physical properties of the compound were as follows:

Aufarbeitung

  1. temperatureThe reaction solution was mildly heated
  2. temperatureThe reaction solution was further heated
  3. temperatureunder reflux for an additional 30 minutes
  4. washThe resulting mixture was washed successively with water
  5. dry with materiala saturated aqueous solution of sodium carbonate and water, and then dried over magnesium sulfate
  6. concentrationThe resulting organic solution was concentrated under reduced pressure
  7. customThe residue was then purified through silica gel column chromatography (75 to 230 mesh; eluent: benzene)

Quellen und Nachweise

ORD-Eintrag
ord-b04ebeed25cb4373ae090a505820565d
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229238

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