Phosgene → Methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate

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A solution of methyl 2-(aminosulfonyl)-4-ethoxybenzoate (7.56 g. 29.2 mmol). n-butyl isocyanate (3.29 mL. 29.2 mmol). and 1.4-diaza[2.2.2]bicyclooctane (0.13 g 1.2 mmol) in mixed xylenes was heated at reflux for 10 minutes. Phosgene was then added at such a rate that the internal temperature stayed at 133° C. or above. When consumption of phosgene ceased, the solution was cooled to room temperature and then filtered under nitrogen. Rotary evaporation gave methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate as a cloudy yellow oil (8.2 g). This was used immediately without further purification or characterization.

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