Water → HCID 22661875, compound

To a mixture of 2-[5-chloro-2-(isothiazol-5-ylmethoxy)benzyl]isoindole-1,3-dione (464 mg, 1.20 mmol), 2-propanol (20 mL), water (2.5 mL), and THF (25 mL) was added NaBH4 (295 mg, 7.80 mmol). The reaction was stirred at room temperature for 16 h. The organic solvent was then removed by rotary evaporation and the resulting oil was taken up in CH2Cl2 (50 mL). The organic layer was washed with water (50 mL), saturated aqueous NaCl (50 mL), dried over NaSO4, filtered, and concentrated on a rotary evaporator. This material was taken up in 2-propanol (20 mL), glacial acetic acid (1.2 mL), and water (1.0 mL) and the reaction was heated to 80° C. in a sealed tube for 24 h. The organic solvent was then removed by rotary evaporation and the resulting oil was taken up in CH2Cl2 (50 mL). The organic layer was washed with water (50 mL), saturated aqueous NaCl (50 mL), dried over NaSO4, filtered, and concentrated on a rotary evaporator to afford the title compound.

1. customThe organic solvent was then removed by rotary evaporation
2. washThe organic layer was washed with water (50 mL), saturated aqueous NaCl (50 mL)
3. dry with materialdried over NaSO4
4. filtrationfiltered
5. concentrationconcentrated on a rotary evaporator
6. temperatureglacial acetic acid (1.2 mL), and water (1.0 mL) and the reaction was heated to 80° C. in a sealed tube for 24 h
7. customThe organic solvent was then removed by rotary evaporation
8. washThe organic layer was washed with water (50 mL), saturated aqueous NaCl (50 mL)
9. dry with materialdried over NaSO4
10. filtrationfiltered
11. concentrationconcentrated on a rotary evaporator

ORD record

ord-0dfa20257a1b4bd88829e8f771720bda

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06803457B1