Chloroform → 1-Sulfonylurea

Participants

Reaction Steps

A sulfonylurea derivative (SUNCS) is synthesized in preparation for making another sulfonylurea-containing initiator polymer. The preparation of SUNCS is achieved according to the synthetic scheme as illustrated in FIG. 3. 4-(2-Amino-ethyl)benzenesulfonamide (AEBS) is first dissolved in acetonitrile (or chloroform). In step 1 the AEBS solution is reacted with carbon disulfide (CS2) and dicyclohexylcarbodiimide (DCC). Dicyclohexylurea (DCU) product is removed from sulfamoyl-isothiocyanate (S-NCS) by filtration. The solvents are then removed to give the S-NCS intermediate. In step 2 the S-NCS, cyclohexyl isocyanate, and tetrabutylammonium bromide (TBAB) are placed in a glass vessel with tetrahydrofuran (THF) and the mixture is stirred under an inert dry atmosphere during the slow addition of sodium hydride (NaH). The SUNCS product (Compound IV, also shown in Table I) is then isolated and purified by flash chromatography.

Provenance & Evidence