Ammonia → N-(4-Bromophenyl)methanesulfonamide

A stirred solution of 4-bromoaniline (1.0 g, 5.81 mmol) and triethylamine (2.43 mL, 17.4 mmol) in DCM (10 mL) at 0° C. is treated with methanesulfonyl chloride (0.47 mL, 6.10 mmol) over 5 minutes via syringe. The reaction is then warmed to RT and stirred 1 h. Analysis by LC/MS at this juncture indicated the reaction mixture contained unreacted starting material, the desired mono-sulfonamide and undesired bis-sulfonamide in a 1:1:1 ratio. Thus more triethylamine (5.0 mL, 35.9 mmol) and methanesulfonyl chloride (1.0 mL, 12.9 mmol) is added and the reaction stirred at RT a further 2 h. On confirmation by LC/MS that all the starting aniline had been converted to the mono- or bis-sulfonamide, the reaction is diluted with water (15 mL) and extracted into EtOAc (3×25 mL). The combined EtOAc phases are then dried (Na2SO4) and reduced in vacuo. The residue thus obtained is dissolved in THF (50 mL) and MeOH (50 mL) then treated with conc. ammonia solution (75 mL) at RT and stirred 16 h. The reaction mixture is then concentrated in vacuo, diluted with water (50 mL) and extracted into EtOAc (3×25 mL). The combined EtOAc phases are dried (MgSO4) and reduced in vacuo to afford the title compound.

1. stirringthe reaction stirred at RT a further 2 h
2. extractionextracted into EtOAc (3×25 mL)
3. dry with materialThe combined EtOAc phases are then dried (Na2SO4)
4. customThe residue thus obtained
5. stirringstirred 16 h
6. concentrationThe reaction mixture is then concentrated in vacuo
7. additiondiluted with water (50 mL)
8. extractionextracted into EtOAc (3×25 mL)
9. dry with materialThe combined EtOAc phases are dried (MgSO4)

ORD record

ord-97209e7772e14206be0351649e27a2de

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273747B2