Ammonia → 2-Hydroxy-5-sulfamoylbenzoic acid

Temperature

60 °C

Ammonia gas was bubbled through a solution of 107 mmol 5-chlorosulfonyl-2-hydroxy-benzoic acid in 250 ml acetone at 0° C. for 2 h. Argon gas was then bubbled through the reaction mixture for 1 h to purge excess ammonia. The mixture was then diluted with water, the pH adjusted to pH 14 by addition of 5 M aq NaOH solution, and the mixture was then extracted with ether/ethyl acetate (1:1). The aqueous phase was acidified with concentrated HCl, saturated with NaCl, and extracted twice with THF. The combined THF extracts were dried with Na2SO4. Evaporation of the solvent in vacuo followed by drying of the residue by heating at 60° C. overnight in vacuo yielded the title compound.

1. customArgon gas was then bubbled through the reaction mixture for 1 h
2. customto purge excess ammonia
3. additionThe mixture was then diluted with water
4. additionthe pH adjusted to pH 14 by addition of 5 M aq NaOH solution
5. extractionthe mixture was then extracted with ether/ethyl acetate (1:1)
6. extractionextracted twice with THF
7. dry with materialThe combined THF extracts were dried with Na2SO4
8. customEvaporation of the solvent in vacuo
9. customby drying of the residue

ORD record

ord-c6bc289edf64425c8c4f081d206499f2

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07319099B2