Acetyl chloride → HCID 13922843, compound

Temperature

-5 °C

A solution of 5-hydroxy-2-sulfamoylbenzo[b]thiophene (4.00 g, 0.017 m) in acetone (70 ml) was cooled to -5° C., triethylamine (1.92 g, 0.019 m) was added, followed by the dropwise addition of a solution of acetyl chloride (1.49 g, 0.019 m) in acetone (10 ml) over 15 minutes, maintaining the temperature at -5° to -3° C. After stirring at -5° C. for 21/4 hours, the mixture was filtered and the solid was washed with acetone. The combined filtrate and washings were concentrated under reduced pressure, the residue was dissolved in ethyl acetate (7.5 ml) washed with water (2×20 ml), dried and evaporated under reduced pressure. The residue was crystallized from 1,2-dichloroethane to yield 4.01 g (87%) of product melting at 129°-132° C. An analytical sample melted at 131.5°-133° C. after recrystallization from 1,2-dichloroethane.

1. temperaturemaintaining the temperature at -5° to -3° C
2. filtrationthe mixture was filtered
3. washthe solid was washed with acetone
4. concentrationThe combined filtrate and washings were concentrated under reduced pressure
5. dissolutionthe residue was dissolved in ethyl acetate (7.5 ml)
6. washwashed with water (2×20 ml)
7. customdried
8. customevaporated under reduced pressure
9. customThe residue was crystallized from 1,2-dichloroethane

ORD record

ord-f254addc0fbe4038a0c998137867c5d2

Source dataset

uspto-grants-1987_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04668697