Hydrochloric Acid → HCID 585041, compound

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).

1. customTo the obtained reaction mixture
2. stirringby stirring at 0° C. for further two hours
3. additionmixed
4. customthe organic layer was separated
5. extractionthe aqueous layer was extracted once with ethyl acetate (3 mL)
6. concentrationconcentrated under reduced pressure to dryness
7. additionTo the obtained residue, ethyl acetate (3 mL) was added
8. additionthoroughly mixed
9. filtrationthe insoluble matter was filtered off
10. concentrationThen, the filtrate was concentrated under reduced pressure to dryness

ORD record

ord-fa7862d6c40f486fb41b2b2181c4fc28

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367857B2