Methylamine → 5-Methylsulfamoyl-2-trifluoromethoxy-benzoic acid

To a solution of 5-Chlorosulfonyl-2-trifluoromethoxy-benzoic acid (0.15 g) in dichloromethane (1.5 ml) was added a solution of methylamine in methanol (8M, 0.31 mL), and the reaction mixture was stirred for 2 minutes after precipitation was complete. The reaction mixture was then concentrated in vacuo and the residue was dissolved in 1N NaOH (2 mL) and extracted with diethylether. The aqueous phase was then acidified using 3 N hydrochloric acid solution (2 mL), and the solution was extracted with dichloromethane (2×10 mL). The combined organic phases were dried with sodium sulfate and concentrated in vacuo to yield the title compound as a white solid (0.12 g). MS (m/e): 298.0 (M−H, 100%).

1. customafter precipitation
2. concentrationThe reaction mixture was then concentrated in vacuo
3. dissolutionthe residue was dissolved in 1N NaOH (2 mL)
4. extractionextracted with diethylether
5. extractionthe solution was extracted with dichloromethane (2×10 mL)
6. dry with materialThe combined organic phases were dried with sodium sulfate
7. concentrationconcentrated in vacuo

ORD record

ord-ba6b1ebf4b104ac381dfa98fdd99a149

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605163B2