Hydrochloric Acid → HCID 15396781, compound

Participants

Reaction Steps

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 3-amino-4-methylbenzoic acid (0.23 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 26 hours. The obtained reaction mixture was dropwise added to a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) over a period of two 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 concentrated under reduced pressure to dryness. To the residue, ethyl acetate (6 mL) and water (1 mL) were added, and the organic layer was concentrated under reduced pressure to dryness to obtain 3-isothiocyanato-4-methylbenzoic acid as a ocher solid (0.26 g, yield: 91%, HPLC purity: 95%, HPLC retention time: 3.9 min). LC-MS ES-192 (retention time: 4.3 min, condition 1).

Provenance & Evidence