Ethanol → N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamide

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide (5.36 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol), potassium carbonate (5.1 g, 36.8 mmol), water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol) were combined and the mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was then added. The mixture was heated at 60° C. for about 2 hours, then heated at 70° C. for 30 minutes. The mixture was then cooled to room temperature and water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered through Celite® and concentrated to yield the crude product as a red solid (8.6 g). The solid material was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield the crude product as a reddish-brown solid (6.2 g). The solid material was again triturated with EtOAc, filtered, and rinsed with EtOAc to yield 4′-methybiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide as a light brown solid (4.6 g; 96.2% purity).

Provenance & Evidence