Formic Acid → HCID 178506084, compound

A solution of 4-chloro-3,5-bis(trifluoromethyl)benzothioamide (1 g) in DMF (10 mL) was treated with hydrazine hydrate (0.32 g, 2.0 eq.) and the reaction mixture was stirred at room temperature for 1 h before adding formic acid (3 mL). The reaction mixture was refluxed at 90° C. for 3 h then cooled to room temperature, poured into aqueous saturated NaHCO3 (slowly, maintaining temperature 25-30° C.) and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (3×50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure (25° C., 20 mmHg) to afford 1.5 g of crude compound. Purification by column chromatography (eluting with 40% EtOAc in hexane) afforded 0.50 g of desired compound (yield: 36%).

1. temperatureThe reaction mixture was refluxed at 90° C. for 3 h
2. temperaturethen cooled to room temperature
3. temperaturemaintaining temperature 25-30° C.) and
4. extractionextracted with EtOAc (3×100 mL)
5. washThe combined organic extracts were washed with brine (3×50 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure (25° C., 20 mmHg)
9. customto afford 1.5 g of crude compound
10. customPurification
11. washby column chromatography (eluting with 40% EtOAc in hexane)

ORD record

ord-1cbcf5f96dee46c3b28b70c0e300798a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206158B2