Methyl iodide → HCID 178503864, compound
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[NH:11][C:12]([NH:14][C:15]2[C:19]([CH3:20])=[CH:18][S:17][CH:16]=2)=[S:13])[O:4][CH2:3][CH2:2]1.CI.[C:23](OCC)(=O)C>O1CCCC1>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[NH:11][C:12](=[N:14][C:15]2[C:19]([CH3:20])=[CH:18][S:17][CH:16]=2)[S:13][CH3:23])[O:4][CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
1-(1,4-Dioxaspiro[4.5]dec-6-yl)-3-(4-methylthiophen-3-yl)thiourea (393 mg) was dissolved in absolute tetrahydrofuran (8.5 ml), and a solution of methyl iodide (179 mg) in absolute tetrahydrofuran (0.5 ml) was added. The mixture was then stirred at 70° C. in sand bath for 2 days. Ethyl acetate was then added to the reaction mixture, and the mixture was washed twice with water. The organic phase was dried over magnesium sulfate and the solvent was removed after filtration. The residue was purified by preparative chromatography and the product-containing fractions were combined, freed from acetonitrile, made basic and extracted three times with ethyl acetate. The organic phases were combined, dried (MgSO4) and filtered. This gave 59 mg of the desired product which was used directly for the next step.
Workup
- washthe mixture was washed twice with water
- dry with materialThe organic phase was dried over magnesium sulfate
- customthe solvent was removed
- filtrationafter filtration
- customThe residue was purified by preparative chromatography
- extractionextracted three times with ethyl acetate
- dry with materialdried (MgSO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-520929116c564d9d8bcec15e0820c7af
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763643B2
Reaction notes
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