Water → HCID 68062528, compound

To a solution of 4-methyl-N-(methylsulfonyl)benzamide (Preparation 55, 550 mg, 2.58 mmol) in tetrachloromethane (10 mL) was added N-bromosuccinimide (459 mg, 2.58 mmol) and diphenylperoxyanhydride (62.5 mg, 0.258 mmol) and the mixture was heated at reflux under nitrogen for 4 hours. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with DCM (50 mL). The organic layer was dried over magnesium sulphate and evaporated in vacuo to yield a cream solid. The solid was re-dissolved in trichloromethane (10 mL), diphenylperoxyanhydride (62 mg, 0.25 mmol) and N-bromosuccinimide (300 mg, 1.69 mmol) were added and the mixture heated at reflux for 6 hours then cooled to room temperature and evaporated in vacuo. The resulting residue was partitioned between DCM (50 mL) and water (50 mL), the aqueous further extracted with DCM (50 mL) and the combined organics dried over magnesium sulphate and concentrated in vacuo to yield a cream solid (625 mg). A portion of this material was purified by silica gel chromatography eluting with 0 to 30% EtOAc in heptane to yield the title compound as a white solid (25 mg).

1. temperaturethe mixture was heated
2. temperatureat reflux under nitrogen for 4 hours
3. extractionextracted with DCM (50 mL)
4. dry with materialThe organic layer was dried over magnesium sulphate
5. customevaporated in vacuo
6. customto yield a cream solid
7. temperaturethe mixture heated
8. temperatureat reflux for 6 hours
9. temperaturethen cooled to room temperature
10. customevaporated in vacuo
11. customThe resulting residue was partitioned between DCM (50 mL) and water (50 mL)
12. extractionthe aqueous further extracted with DCM (50 mL)
13. dry with materialthe combined organics dried over magnesium sulphate
14. concentrationconcentrated in vacuo

ORD record

ord-572751383d58460095847c7a597e282c

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096500B2