Sodium Hydroxide → HCID 68818593, compound

Temperature

0 °C

2-[(4-Fluorophenyl)sulfanyl]aniline (400 mg, 1.6 mmol) was stirred at 0° C. in conc. HCl (4.0 mL) and NaNO2 (130 mg, 1.8 mmol) was added slowly, maintaining 0° C. reaction temperature. After stirring for 1 hour at 0° C., a solution of SnCl2 (610 mg, 3.2 mmol) in 1.5 mL conc. HCl was added. The reaction was brought to rt and stirred for one h. Upon completion, the reaction was basified with 1N aqueous NaOH to pH 12. The reaction mixture was partition between water and CHCl3 and the aqueous layer extracted with CHCl3 (3×20 mL). The combined extracts were washed with brine (20 mL), H2O (20 mL) and dried (Na2SO4) and evaporated to a residue. The residue was taken up in a minimal amount of CHCl3 (10 mL) and 1N HCl-Ether (10 mL) was added. The solvent was evaporated affording 1-{2-[(4-fluorophenyl)sulfanyl]phenyl}hydrazine hydrochloride as a dark semi-solid (327 mg, 76%). 1H NMR (CD3OD, 300 MHz) δ 7.40-7.51 (m, 2H), 7.16-7.25 (m, 2H), 6.95-7.14 (m, 4H) ppm.

1. customreaction temperature
2. customwas brought to rt
3. stirringstirred for one h
4. customThe reaction mixture was partition between water and CHCl3
5. extractionthe aqueous layer extracted with CHCl3 (3×20 mL)
6. washThe combined extracts were washed with brine (20 mL), H2O (20 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated to a residue
9. additionwas added
10. customThe solvent was evaporated

ORD record

ord-e8bcc4cd6ffc47ffbf8dd9b3b74bf61c

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592454B2