Methyl iodide → N-(2,4-dichloro-thiazol-5-yl)-N-methyl-3-methylsulfanyl-propionamide
Reaction equation
[Cl:1][C:2]1[S:3][C:4]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][S:12][CH3:13])=[C:5]([Cl:7])[N:6]=1.[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[Cl:1][C:2]1[S:3][C:4]([N:8]([CH3:15])[C:9](=[O:14])[CH2:10][CH2:11][S:12][CH3:13])=[C:5]([Cl:7])[N:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of N-(2,4-dichloro-thiazol-5-yl)-3-methylsulfanyl-propionamide (596 mg, 2.2 mmol) in DMF (11 mL) stirring at 25° C. was added K2CO3 (365 mg, 2.64 mmol) and iodomethane (375 mg, 1.2 mmol), the solution was stirred at 25° C. for 20 h. The solution was diluted with 50 mL H2O and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with H2O (3×20 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as a clear oil (273 mg, 44%): 1H NMR (300 MHz, CDCl3) δ 3.23 (s, 3H), 2.79 (t, J=7.2 Hz, 2H), 2.52 (t, J=7.2 Hz, 2H), 2.09 (s, 3H); ESIMS m/z 285.1 (M+1).
Workup
- extractionextracted with ethyl acetate (3×20 mL)
- washThe combined organic extracts were washed with H2O (3×20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
- customThe crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-154d733d5ba247edbedda50a63dbcbc5
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09357780B2
Reaction notes
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