Potassium Hydroxide → 3,5-bis-dimethylthiocarbamoyloxybenzoic acid methyl ester

Temperature

0 °C

To a stirred solution of 3,5-dihydroxybenzoic acid methyl ester (10.0 g, 59.5 mmol) in DMF (200 mL) at 0° C. was added NaH (60% dispersion in mineral oil, 5.00 g, 125 mmol, 2.1 eq.) in small portions. The reaction mixture was stirred at 0° C. for 15 min then warmed to room temperature. After 1 h, the reaction mixture was cooled to 0° C. and then added dimethylthiocarbamoyl chloride (14.7 g, 119 mmol). Following the addition, the reaction was stirred for 45 min at 0° C., then for 30 min at room temperature and then heated to 80° C. After 2 h at 80° C., the reaction mixture was cooled to room temperature and then added to 1% aqueous KOH (500 mL). The resulting mixture was extracted with ethyl ether (2×500 mL). The organic layer was washed with H2O (500 mL), brine (300 mL), dried over MgSO4 and concentrated in vacuo to afford 3,5-bis-dimethylthiocarbamoyloxybenzoic acid methyl ester (13.0 g). This material was used without further purification.

1. temperaturethen warmed to room temperature
2. waitAfter 1 h
3. temperaturethe reaction mixture was cooled to 0° C.
4. additionthe addition
5. stirringthe reaction was stirred for 45 min at 0° C.
6. waitfor 30 min at room temperature
7. temperatureheated to 80° C
8. waitAfter 2 h at 80° C.
9. temperaturethe reaction mixture was cooled to room temperature
10. extractionThe resulting mixture was extracted with ethyl ether (2×500 mL)
11. washThe organic layer was washed with H2O (500 mL), brine (300 mL)
12. dry with materialdried over MgSO4
13. concentrationconcentrated in vacuo

ORD record

ord-f61fe97ace3247e383b854a5e2a40399

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691843B2