Ammonium Chloride → 1-[5-Amino-3-chloro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-phenyl]-ethanone

To a solution of 1-[3-chloro-5-nitro-2-(5-methyl-benzothiazol-2-ylsulfanyl)-phenyl]-ethanone (264) (3.87 g, 10.2 mmol) in 2:2:1 of EtOH/THF/H2O, was added ammonium chloride (Aldrich 2.74 g, 51.2 mmol) and iron powder (Aldrich, 2.87 g, 51.2 mmol). The mixture was refluxed for 3 hours. The mixture was filtered through Celite pad while it was hot, washed the Celite pad with EtOAc. The filtrate was diluted with saturated aqueous NaHCO3 solution and was extracted 3× with EtOAc (150 mL). The organic layers were combined and washed twice with a brine solution (100 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was chromatographed (0-15% EtOAc in CH2Cl2) to yield 2.42 g (68%) of compound 276 as a pale yellow solid.

1. temperatureThe mixture was refluxed for 3 hours
2. filtrationThe mixture was filtered through Celite pad while it
3. washwashed the Celite pad with EtOAc
4. additionThe filtrate was diluted with saturated aqueous NaHCO3 solution
5. extractionwas extracted 3× with EtOAc (150 mL)
6. washwashed twice with a brine solution (100 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under vacuum
9. customThe crude solid was chromatographed (0-15% EtOAc in CH2Cl2)

ORD record

ord-4c71710c170542ea8f7cdeabb5098409

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06770648B2