Triethylamine → 2-Methylsulfonyloxyimino-4-phenyl-but-3-enenitrile
Reaction equation
[OH:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]#[N:5].C(=NO)C=CC1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C(N(CC)CC)C>O1CCCC1.O>[CH3:25][S:26]([O:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]#[N:5])(=[O:28])=[O:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
3.44 g (0.02 mol) of 2-hydroxyimino-4-phenyl-but-3-enenitrile, (mp 127-129° C., prepared from cinnamaldoxime according to C. Trione et al, J. Org. Chem. 1993, 58, 2075) are dissolved in 20 ml of anhydrous tetrahydrofuran and cooled to 0° C. Methanesulfonyl chloride (1.7 ml, 0.022 mol) is added at once, followed by triethylamine (4.2 ml, 0.03 mol) dropwise over 15 min, keeping the temperature of the mixture at 5° C. The mixture is then stirred at 25° C. for two hours, and poured into 150 ml of iced water. The off-white precipitate is washed with ether, dried and recrystallyzed from 70 ml of ethanol, yielding 2.74 g (55%) of 2-methylsulfonyloxyimino-4-phenyl-but-3-enenitrile as colorless crystals, mp. 144-148° C. No attempt is made to recover more material from the ether extract.
Workup
- customat 5° C
- washThe off-white precipitate is washed with ether
- customdried
Sources & evidence
- ORD record
- ord-6e864a295320474598126a5572040936
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06703182B1
Reaction notes
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