Hydrochloric Acid → 3-Nitrobenzene-1-thiol

(Cashman, J. R. et al. Chem. Res. Toxicol., 1989, 2:392-399). To a solution of m-nitrobenzene disulfide (300 mg, 0.97 mmol) in anhydrous THF (2 mL) was added solid NaBH4 (140 mg, 3.4 mmol) in small portions. The resulting mixture was stirred at room temperature under an inert atmosphere. After 2 hr, the reaction mixture was cooled in an ice bath, and then about 5 mL of ice water was added to the mixture. The resulting mixture was acidified with HCl (1 M), then extracted with CH2Cl2 (10 mL). The organic layer was then washed with water (10 mL), then brine (10 mL), dried over MgSO4, and concentrated in vacuo to give 43 (248 mg, 83%) as a pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ 8.10 (d, J=2.0 Hz, 1H); 7.97 (dd, J=8.0, 2.0 Hz, 1H); 7.54 (d, J=8.0 Hz, 1H); 7.38 (t, J=8.0 Hz, 1H); 3.68 (s, 1H); 13C NMR (CDCl3, 100 MHz): δ 134.9, 130.0=, 123.9, 120.7.

1. temperaturethe reaction mixture was cooled in an ice bath
2. extractionextracted with CH2Cl2 (10 mL)
3. washThe organic layer was then washed with water (10 mL)
4. dry with materialbrine (10 mL), dried over MgSO4
5. concentrationconcentrated in vacuo

ORDレコード

ord-2a11c3b5eec6431c9ee8d84a7d537e89

出典データセット

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08722937B2