Sodium methanethiolate → HCID 86064723, compound
Reaction equation
CS(O[CH2:6][CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[CH3:19][S-:20].[Na+]>CN(C)C=O>[CH3:19][S:20][CH2:6][CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (28 g, 99 mmol) and sodium thiomethoxide (8.3 g, 119 mmol) in N,N-dimethylformamide (DMF, 200 mL) was heated to 80° C. and maintained at that temperature until analysis by thin layer chromatography (TLC) indicated that the starting material had been consumed. The reaction mixture was allowed to cool to ambient temperature and was then quenched with water (200 mL). The reaction mixture was extracted with diethyl ether (2×200 mL). The combined extracts were washed sequentially with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to provide 22.5 g of tert-butyl 2-[2-(methylthio)ethoxy]ethylcarbamate as a light yellow oil.
Workup
- temperaturemaintained at that temperature until analysis by thin layer chromatography (TLC)
- customhad been consumed
- temperatureto cool to ambient temperature
- customwas then quenched with water (200 mL)
- extractionThe reaction mixture was extracted with diethyl ether (2×200 mL)
- washThe combined extracts were washed sequentially with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2956082bb87a4100ad483657a6379cc9
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939526B2
Reaction notes
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