Hydrochloric Acid → HCID 19820837, compound

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 6-aminohexanoic acid (0.20 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 44 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 5 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 obtained residue, a solvent mixture of hexane (3 mL) and ethyl acetate (3 mL) was added and thoroughly mixed, and an insoluble matter was filtered off. Then, the filtrate was concentrated under reduced pressure to dryness to obtain 6-isothiocyanatohexanoic acid as an orange oil (0.26 g, yield: 98%, and 1H-NMR spectrum showed no distinct by-product). LC-MS ES-172 (retention time: 19.3 min, condition 3).

1. customThe obtained reaction mixture
2. stirringby stirring at 0° C. for further two hours
3. additionmixed
4. customthe organic layer was separated
5. concentrationconcentrated under reduced pressure to dryness
6. additionTo the obtained residue, a solvent mixture of hexane (3 mL) and ethyl acetate (3 mL)
7. additionwas added
8. additionthoroughly mixed
9. filtrationan insoluble matter was filtered off
10. concentrationThen, the filtrate was concentrated under reduced pressure to dryness

ORD record

ord-286960bb15444bc7a3d7f652ad52e862

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367857B2