Potassium ethanethioate → HCID 60134444, compound
Reaction equation
CS(O[CH2:6][CH2:7][N:8]([CH3:16])[CH2:9][C:10]([CH3:15])([N+:12]([O-:14])=[O:13])[CH3:11])(=O)=O.[C:17]([O-:20])(=[S:19])[CH3:18].[K+]>C(#N)C>[C:17](=[O:20])([S:19][CH2:6][CH2:7][N:8]([CH3:16])[CH2:9][C:10]([CH3:11])([N+:12]([O-:14])=[O:13])[CH3:15])[CH3:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-(Methyl(2-methyl-2-nitropropyl)amino)ethyl methanesulfonate (12.0 g, 47.2 mmol) was dissolved into anhydrous acetonitrile (200 mL) and solid potassium thioacetate (5.93 g, 1.1 equiv, 51.9 mmol) was added to flask in one portion. The suspension was heated at 50° C. for 4 h. The red slurry was filtered and the solid washed with ethyl acetate (3×150 mL). The filtrate was concentrated to a red brown oil and purified on an ISCO purification system using a 120 g SiO2 column and the following gradient: isocratic 20% EA in hexanes (5 min) and a gradient to 60% EA in hexanes (15 min). The desired fractions were collected and concentrated to give a red oil (6.83 g, 61.8%). 1H NMR (CDCl3, 400 MHz): δ 1.56 (s, 6H), 2.32 (s, 3H), 2.33 (s, 3H), 2.61-2.65 (m, 2H), 2.89-2.93 (m, 4H). LRMS (ESI+) for C9H18N2O3S (234.1); Found: 235 (MH+).
Workup
- additionwas added to flask in one portion
- filtrationThe red slurry was filtered
- washthe solid washed with ethyl acetate (3×150 mL)
- concentrationThe filtrate was concentrated to a red brown oil
- custompurified on an ISCO purification system
- custom20% EA in hexanes (5 min)
- customto 60% EA in hexanes (15 min)
- customThe desired fractions were collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ed9bd806e4d74791862185ef2955c6ed
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278482B2
Reaction notes
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