Chlorosuccinimide → HCID 54468912, compound

To a solution of thiophen-2-yl-sulfanyl acetic acid ethy (0.52 g, 2.6 mmol) in 25 mL of CH2Cl2 is added N-chlorosuccinimide (0.35 g, 2.6 mmol). The solution is stirred for 10 minutes. After this time, 1 drop of TFA is added. The solution is stirred for 16 hours. The reaction mixture is then diluted with 25 mL of CH2Cl2. The resulting solution is washed with 1N NaOH and a saturated NaCl solution. The organic layer is dried over MgSO4, filtered and concentrated. The resulting product is obtained as an oil which is determined to contain 45% of the desired product. The oil is then dissolved in 60 mL of 1:1:1 THF:MeOH:H2O. To the solution is added lithium hydroxide monohydrate (1.26 g, 30 mmol). The solution is stirred for 16 hours. After this time, the solution is acidified to pH=3 with 1N HCl. The aqueous solution is washed with H2O and saturated NaCl solution. The solution is extracted with EtOAc/CH2Cl2 (2:1). The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude product is purified by column chromatography eluting with 20% MeOH:Et2O to give the product as a white solid (0.4 g, 1.9 mmol). MS (EI): m/z 208, 210 (M+), Cl pattern.

1. stirringThe solution is stirred for 16 hours
2. washThe resulting solution is washed with 1N NaOH
3. dry with materialThe organic layer is dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe resulting product is obtained as an oil which

ORD record

ord-d1728b5067494128b8278b574a9dea70

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2