Phosgene → 2-[(Dimethylsulfamoyl)methyl]benzene-1-sulfonyl isocyanate

Participants

Reaction Steps

A solution of 14.0 g of the product of Example 4, 5.0 g of n-butyl isocyanate and 0.1 g of DABCO in 90 ml of mixed xylenes was heated to 136°. To this solution was added 3.6 ml of liquid phosgene over a 2 hour period to maintain the temperature between 125° and 136°. The temperature was kept at 130° for 1/2 hour after the addition. The solution was cooled, and filtered under a nitrogen atmosphere and concentrated at 60°-70° in vacuo to give 16.0 g of crude 2-[(dimethylamino)sulfonylmethyl]benzenesulfonyl isocyanate as a moisture sensitive oil. An infrared peak at 2200 cm-1 confirmed the presence of the --SO2NCO group.

Provenance & Evidence