Carbon Disulfide → HCID 20293330, compound

Participants

Reaction Steps

To a solution of methyl 2-methoxy-4-methyl-5-aminobenzoate (975 mg) in tetrahydrofuran (5 ml) are added triethylamine (1.52 g) and carbon disulfide (1.14 g), and the resultant mixture is stirred at room temperature for 2.5 hours. Ethyl chlorocarbonate (1.63 g) is added to the mixture, which is stirred for additional 20 minutes at room temperature. A solution of sodium hydroxide (1.2 g) in water (32 ml) is added to the mixture, which is stirred for 15 minutes. The reaction mixture is mixed with an excess amount of water and shaken with methylene chloride. The organic layer is dried over Glauber's salt and the solvent is evaporated. The residue is dissolved in methylene chloride and chromatographed on a column of silica gel. Evaporating the solvent from the elution, the residue is dissolved in isopropyl ether and n-hexane is added thereto. The precipitated crystals are filtered to give 3-methoxycarbonyl-4-methoxy-6-methylphenyl isothiocyanate (952 mg) as crystals melting at 86°-87.5° C.

Provenance & Evidence