Acetone → 2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-methylsulfanyl-2-propenenitrile
Reaction equation
C([S:4]([CH2:7][C:8]#[N:9])(=[O:6])=[O:5])CC.C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([N:24]=[C:25]=[S:26])[CH:21]=[CH:22][CH:23]=1.[CH3:27]I.[CH3:29][C:30]([CH3:32])=O>>[CH:30]([S:4]([C:7](=[C:25]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=1)[S:26][CH3:27])[C:8]#[N:9])(=[O:6])=[O:5])([CH3:32])[CH3:29]Participants
Procedure
A solution of 2-propanesulfonylacetonitrile (2.0 g, 13.6 mmol) in dry acetone (25 ml) was stirred while dry potassium carbonate (1.28 g, 9.28 mmol) and 3-methoxyphenyl isothiocyanate (2.36 g, 14.3 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (2.54 ml, 40.8 mmol) was added to the filtrate, and stirring was continued for 60 h. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 4.40 g (99%) of the title compound as yellow crystals. Mp 107-110° C. 1H NMR (200 MHz, CDCl3): δ=1.44 (d, 6H), 2.22 (s, 3H), 3.36 (heptet, 1H), 3.83 (s, 3H), 6.81 (m, 1H), 6.85 (dd, 1H), 6.87 (dd, 1H), 7.32 (dd, 1H), 9.91 (br s, 1H).
Workup
- additionwere added
- filtrationExcess of potassium carbonate was filtered off
- stirringstirring
- waitwas continued for 60 h
- customThe mixture was evaporated
- dissolutionthe residue was dissolved in dichloromethane
- extractionextracted with water and brine
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-47ce245c26fe4adeb3cd1bd6da46a983
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365609B1
Reaction notes
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