Hydrochloric Acid → 3,5-Diisothiocyanatobenzoic acid

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Reaction Steps

Carbon disulfide (0.54 mL, 9.1 mmol) was added to a mixture comprising 3,5-diaminobenzoic acid (0.23 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.84 mL, 6.0 mmol), followed by stirring at room temperature for 31 hours. To the obtained reaction mixture, a tetrahydrofuran (2.0 mL) solution of iodine (0.82 g, 1.6 mmol) was dropwise added over a period of 5 minutes at 0° C., followed by stirring at 0° C. for further 2.5 hours. Thereafter, 1M hydrochloric acid (1.5 mL) and sodium sulfite (76 mg, 0.30 mmol) were added and mixed. Then, ethyl acetate (6 mL) was added, and the organic layer was separated and concentrated under reduced pressure to dryness. To the obtained residue, ethyl acetate (6 mL), water (3 mL) and sodium hydrogencarbonate (10 mg, 0.12 mmol) were added, and the organic layer was concentrated under reduced pressure to dryness. To the obtained residue, chloroform (6 mL) was added and thoroughly mixed, and then an insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to dryness, and then, to the obtained residue, chloroform (6 mL) and hexane (1 mL) were added and thoroughly mixed. Then, the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to dryness to obtain 3,5-diisothiocyanatobenzoic acid as a colorless solid (0.31 g, yield: 86%, HPLC purity: 97%, HPLC retention time: 5.3 min). LC-MS ES-235 (retention time: 4.6 min, condition 1).

Provenance & Evidence