Methyl iodide → 4-amino-N,N-dimethyl-2-oxo-3-pentenesulfonamide
Reaction equation
[NH2:1][C:2]([CH3:12])=[CH:3][C:4](=[O:11])[CH2:5][S:6]([NH:9][CH3:10])(=[O:8])=[O:7].CI.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]([CH3:12])=[CH:3][C:4](=[O:11])[CH2:5][S:6]([N:9]([CH3:15])[CH3:10])(=[O:7])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3.8 g of 4-amino-N-methyl-2-oxo-3-pentenesulfonamide and 1.9 ml of methyl iodide in 50 ml of dimethylformamide was treated with 6 g of finely ground dry potassium carbonate and the mixture was thereupon stirred intensively at room temperature under argon for 6 hours. The organic salts were then filtered off, rinsed with methylene chloride and the filtrate was concentrated to dryness under reduced pressure. The residue was partitioned between water and methylene chloride, the organic phase was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The solid product was recrystallized from isopropanol, whereby there were obtained 2.5 g of 4-amino-N,N-dimethyl-2-oxo-3-pentenesulfonamide in the form of colorless crystals, m.p. 137°-140°.
Workup
- filtrationThe organic salts were then filtered off
- washrinsed with methylene chloride
- concentrationthe filtrate was concentrated to dryness under reduced pressure
- customThe residue was partitioned between water and methylene chloride
- washthe organic phase was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over sodium sulfate
- customevaporated to dryness
- customThe solid product was recrystallized from isopropanol
Sources & evidence
- ORD record
- ord-5a187b194daa452a8d923ae5a7a10ca6
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04742069
Reaction notes
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