Stannous Chloride → HCID 89156686, compound

Temperature

80 °C

To a mixture of 4-nitro-N-(2-(trifluoromethoxy)phenyl)benzenesulfonamide (2.62 g, 7.23 mmol) in EtOH (60 mL) was added Tin (II) chloride dehydrate (8.16 g, 36.2 mmol). The reaction mixture was stirred for 4 h at 80° C. LC-MS and TLC analyses indicated that the reaction was completed. The mixture was cooled down to room temperature. The EtOH was removed via vacuo and the residual was taken up in EtOAc (100 mL), followed by the addition of 2N NaOH (40 mL to make basic). After stirring vigorously for 1 h, the precipitates were filtered through celite and washed with EtOAc. The filtrate layers were separated. The organic layer was washed with 1N NaOH (optional), then water and brine, dried (Na2SO4), filtered, and concentrated. The crude product (brown residue, 1.42 g) was subjected a column purification on BioTage (0-6% MeOH in DCM) to yield a desired product (1.23 g, 51% yield).

1. temperatureThe mixture was cooled down to room temperature
2. customThe EtOH was removed via vacuo
3. additionfollowed by the addition of 2N NaOH (40 mL to make basic)
4. stirringAfter stirring vigorously for 1 h
5. filtrationthe precipitates were filtered through celite
6. washwashed with EtOAc
7. customThe filtrate layers were separated
8. washThe organic layer was washed with 1N NaOH (optional)
9. dry with materialwater and brine, dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customa column purification on BioTage (0-6% MeOH in DCM)

ORD record

ord-5dbd1ccf68304e2ca35fad3a56e55735

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169209B2