Carbamate → HCID 21251132, compound

To a solution of methyl 3-chloro-4-dimethylcarbamoylthiophenylacetate (8.5 g, 0.0295 mol) in methanol (30 mL) was added 25% NaOMe in methanol (7.0 mL, 0.034 mol). The reaction was heated to reflux for 2 h. TLC analysis shows residual starting carbamate. Additional NaOMe/MeOH (1.0 mL) was added and the mixture stirred an additional 30 min at reflux. After cooling to ambient temperature, the thiolate solution was added dropwise to a solution of 1,3-dibromopropane (12 mL, 0.12 mol) in methanol (30 mL). The resulting solution was refluxed for 3 h then cooled to ambient temperature, After standing overnight, the reaction was quenched by pouring into ice water. After adjusting to pH1 with conc. HCl, the aqueous solution was extracted with EtOAc (0.2 L then 2×0.1 L). The combined organics were washed with water, brine, dried over anhyd. MgSO4, filtered, and concentrated. The residue was chromatographed over silica gel with 10% of ethyl acetate in hexane to afford the title compound.

1. temperatureThe reaction was heated
2. temperatureto reflux for 2 h
3. temperatureat reflux
4. temperatureThe resulting solution was refluxed for 3 h
5. temperaturethen cooled to ambient temperature
6. waitAfter standing overnight
7. customthe reaction was quenched
8. additionby pouring into ice water
9. extractionthe aqueous solution was extracted with EtOAc (0.2 L
10. washThe combined organics were washed with water, brine
11. customdried over anhyd
12. filtrationMgSO4, filtered
13. concentrationconcentrated
14. customThe residue was chromatographed over silica gel with 10% of ethyl acetate in hexane

ORD record

ord-98c30212f3d144e198e0f6af38cc851d

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06200998B1