Hydrochloric Acid → HCID 89705463, Verbindung

To a solution of methyl 4-amino-5-(benzylthio)-3-fluoro-2-((2-chlorophenyl)amino)benzoate (2.50 g, 5.99 mmol) in acetic acid (60 mL) was added con. HCl (8 mL). The resultant was stirred at ambient temperature for 1 h. A solution of NaNO2 (0.45 g, 6.58 mmol) in water (10 mL) was added dropwisely at 0° C. in 20 min. After stirring for 3 h, the reaction was treated with saturated NaHCO3 (aq.) till the solution was neutral. The aqueous layer was extracted with ethyl acetate (30 mL×3). The combined organic phase was washed with water (30 mL) and brine (30 mL) sequentially, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 5:1, v/v) to give the corresponding product (yellow solid, 1.82 g, 90.1% yield). 1H NMR (400 MHz, CDCl3): δ 8.83 (s, 1H), 8.59 (d, 1H), 7.45 (m, 1H), 7.24 (m, 1H), 6.95 (m, 2H), 4.03 (s, 3H).

1. stirringAfter stirring for 3 h
2. extractionThe aqueous layer was extracted with ethyl acetate (30 mL×3)
3. washThe combined organic phase was washed with water (30 mL) and brine (30 mL) sequentially
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 5:1
8. customv/v) to give the corresponding product (yellow solid, 1.82 g, 90.1% yield)

ORD-Eintrag

ord-cb5e1741762f43e99367134a96501327

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290468B2