Hydrochloric Acid → Benzoic acid, 3-isothiocyanato-

Participants

Reaction Conditions

Reaction Steps

3-aminobenzoic acid (5.00 g, 36.5 mmol) was added to a methylene chloride solution (51 mL) of thiocarbonyldiimidazole (7.8 g, 43.8 mmol) and triethylamine (5.6 mL, 40.2 mmol) at an internal temperature of at most 5° C., followed by stirring at −10° C. for one hour. The mixture was dropped to a separately prepared mixed solution of concentrated hydrochloric acid (11.6 mL, 133.0 mmol) and n-heptane (51 mL) as that the internal temperature became from 20° C. to 30° C., followed by stirring for one hour as it was. Then, the mixture was stirred under cooling with ice for 2 hours, and the obtained colorless solid was collected by filtration, washed with water (20 mL) four times and dried under reduced pressure to obtain 3-isothiocyanatobenzoic acid as a creamy solid (6.01 g, yield: 93%, HPLC purity: 99.8%).

Provenance & Evidence