Toluene → 5-Methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester

関与物質

反応手順

2-Amino-5-methylbenzoic acid methyl ester (122 mg, 0.79 mmol) and triethylamine (0.28 ml, 1.96 mmol) were dissolved in THF (10 ml). A 20% solution of phosgene in toluene (0.74 ml, 1.6 mmol) was added, causing immediate formation of a white precipitate. After 1 h, excess phosgene was purged with a stream of nitrogen, the vented gas being passed through a base scrubber. Thiophenol (81 μl, 0.79 mmol) was added to this crude isocyanate solution, which was then stirred for 1 h. The mixture was filtered to remove triethylamine hydrochloride, the solid being washed with ether. After concentration of the filtrate, the residue was purified by flash chromatography (5% to 10% EtOAc/petrol) to give 5-methyl-2-phenylsulfanylcarbonylaminobenzoic acid, methyl ester: m/z (ES+) 300 (M−H).

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