3-Bromoaniline → 2-(3-Bromophenyl)-1lambda~6~,2-thiazolidine-1,1-dione

To a solution of 3-bromoaniline (1.0 mL, 9.18 mmol) and TEA (2.60 mL, 18.5 mmol) in CH2Cl2 (20 mL) was added 3-chloro-1-propanesulfonyl chloride (1.40 mL, 11.5 mmol) at 0° C. After stirring at room temperature for 16 hr, 3-chloro-1-propanesulfonyl chloride (1.40 mL, 11.5 mmol) and TEA (2.6 mL, 18.5 mmol) was added and the solution stirred at room temperature for 2 hr. The solution was then washed with HCl (1.0 N, aq) and brine, dried over Na2SO4 then concentrated in vacuo. The residue was then taken up in DMF (40 mL) and DBU (4.10 mL, 27.6 mmol) was added. The mixture was stirred at room temperature for 64 hr, diluted with EtOAc, then washed with 1N HCl and brine then concentrated. The residue was purified by silica gel chromatography (EtOAc/hexanes) to give 2-(3-bromophenyl)isothiazolidine 1,1-dioxide as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.50-2.54 (m, 2H), 3.37 (t, J=7.5 Hz, 2H), 3.74 (t, J=7.5 Hz, 2H), 7.22-7.24 (m, 3H), 7.33 (s, 1H).

1. stirringthe solution stirred at room temperature for 2 hr
2. washThe solution was then washed with HCl (1.0 N, aq) and brine
3. dry with materialdried over Na2SO4
4. concentrationthen concentrated in vacuo
5. stirringThe mixture was stirred at room temperature for 64 hr
6. washwashed with 1N HCl and brine
7. concentrationthen concentrated
8. customThe residue was purified by silica gel chromatography (EtOAc/hexanes)

ORD record

ord-981a97dd560543dcb4d53af12fe32e9f

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633175B2