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

Participants

Reaction Conditions

Reaction Steps

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:

Provenance & Evidence