Phosgene → HCID 19024454, compound

Participants

Reaction Steps

A solution of 1.8 g (4.81 mmole) of N-butyl-N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]amine (from Step E) in 35 mL of toluene was cooled to -5° C. and treated with 9.6 mL (24 mmole) of 2.5M sodium hydroxide (aqueous), followed by 7.5 mL (14.5 mmole) of phosgene in toluene. The cold mixture was stirred for 45 minutes and then filtered to remove a white precipitate. The layers of the filtrate were separated, and the toluene phase was concentrated in vacuo to yield 1.21 g (58%) of the title compound as a white solid, mp 128°-129° C.; homogeneous by TLC (3:1 hexane-EtOAc); IR spectrum νCO 1745 cm-1 ; FAB-MS m/e 438 (M+1)+. The 1H NMR spectrum indicated the presence of two rotameric forms.

Provenance & Evidence