Chlorosulfonic acid → HCID 59893774, compound

At −5° C., chlorosulfonic acid (0.22 mL, 3.33 mmol) was slowly added to a chloroform solution (10 mL) of 3,4,5-trimethoxyaniline (1.83 g, 10 mmol). After 1 hour at 25° C., the suspension was filtered, and the solid was washed with CH2Cl2. The residue was dissolved in Na2CO3 solution (0.5M, 20 mL), which was washed with ethyl ether (2×20 mL). The aqueous solution was concentrated to give a solid, which was extracted with boiling ethanol (20 mL). After evaporation of ethanol, the solid (200 mg) was treated with PCl5 (200 mg) in refluxing benzene (15 mL). The precipitate was filtered off and the filtrate was concentrated. The residue was purified by column chromatography (50% EtOAc in hexanes), affording 56 mg (5% yield) of the sulfamoyl chloride as a off-white solid.

1. filtrationthe suspension was filtered
2. washthe solid was washed with CH2Cl2
3. dissolutionThe residue was dissolved in Na2CO3 solution (0.5M, 20 mL)
4. washwhich was washed with ethyl ether (2×20 mL)
5. concentrationThe aqueous solution was concentrated
6. customto give a solid, which
7. extractionwas extracted with boiling ethanol (20 mL)
8. customAfter evaporation of ethanol
9. additionthe solid (200 mg) was treated with PCl5 (200 mg)
10. temperaturein refluxing benzene (15 mL)
11. filtrationThe precipitate was filtered off
12. concentrationthe filtrate was concentrated
13. customThe residue was purified by column chromatography (50% EtOAc in hexanes)

ORD record

ord-d2d70d3ddb5f4cb38e1ae637b1b05024

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06544987B2