Chlorosuccinimide → HCID 19363330, compound

Temperature

0 °C

N-[2-(4-Hydroxyphenyl)ethyl]-4-methoxy-2-methylthio-3-pentyloxybenzamide (85 mg, 0.21 mmol) obtained in Example 2-50, molecular sieve 4A (200 mg) and methylene chloride (1 ml) were mixed, and this mixture was cooled to 0° C. N-Chlorosuccinimide (29.4 mg, 0.22 mmol) was added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered, ethyl acetate (20 ml) was added to the filtrate, and the mixture was washed twice with saturated brine (5 ml). The mixture was dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified twice by column chromatography on silicagel (hene/ethyl acetate=1/1) to give apale-yellow oil. To allow reaction of the residual raw materials, this oil, molecular sieve 4A (200 mg) and methylene chloride (1 ml) were mixed, and cooled to 0° C. N-Chlorosuccinimide (17.4 mg, 0.13 mmol) was added, and the reaction mixture was stirred at room temperature for 2 hours, followed by filtration. Ethyl acetate (20 ml) was added to the filtrate, and the filtrate was washed once with saturated brine (5 ml) and dried over anhydrous magnesium sulfate. Th drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by thin layer chromatography (chloroform/methanol=20/1) to give 2-[2-(4-hydroxyphenyl)ethyl]-6-methoxy-7-pentyloxybenzo[d]isothiazol-3-one (34 mg, 42%) as colorless crystals.

1. filtrationThe reaction mixture was filtered
2. additionethyl acetate (20 ml) was added to the filtrate
3. washthe mixture was washed twice with saturated brine (5 ml)
4. dry with materialThe mixture was dried over anhydrous magnesium sulfate
5. filtrationThe drying agent was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe obtained residue was purified twice by column chromatography on silicagel (hene/ethyl acetate=1/1)
8. customto give apale-yellow oil
9. temperaturecooled to 0° C
10. stirringthe reaction mixture was stirred at room temperature for 2 hours
11. filtrationfollowed by filtration
12. additionEthyl acetate (20 ml) was added to the filtrate
13. washthe filtrate was washed once with saturated brine (5 ml)
14. dry with materialdried over anhydrous magnesium sulfate
15. filtrationTh drying agent was filtered off
16. concentrationthe filtrate was concentrated under reduced pressure
17. customThe obtained residue was purified by thin layer chromatography (chloroform/methanol=20/1)

ORD record

ord-a08fbba990bb4d6e8f6ba5332965e806

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919