Hydrochloric Acid → HCID 585041, compound

Participants

Reaction Steps

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 4-(aminomethyl) benzoic acid (0.23 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 24 hours. To the obtained reaction mixture, a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) was dropwise added over a period of 4 minutes at 0° C., followed by stirring at 0° C. for further two hours. Thereafter, 1M hydrochloric acid (1.5 mL) and sodium sulfite (38 mg, 0.30 mmol) were added and mixed. Then, ethyl acetate (6 mL) was added, and the organic layer was separated and the aqueous layer was extracted once with ethyl acetate (3 mL). The organic layers were combined and concentrated under reduced pressure to dryness. To the obtained residue, ethyl acetate (3 mL) was added and thoroughly mixed, and the insoluble matter was filtered off. Then, the filtrate was concentrated under reduced pressure to dryness to obtain 4-(isothiocyanatomethyl)benzoic acid as a cream-colored solid (0.32 g, yield: 109%, HPLC purity: 88%, HPLC retention time: 3.1 min). LC-MS ES-192 (retention time: 3.5 min, condition 2).

Provenance & Evidence