Reaction equation
[OH:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:5]=[CH:4]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>O1CCCC1>[CH3:25][S:26]([O:1][N:2]=[C:3]1[CH:8]=[CH:7][C:6](=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]#[N:11])[CH:5]=[CH:4]1)(=[O:28])=[O:27]Participants
Procedure
10 g (45 mmol) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are dissolved in 100 ml of tetrahydrofuran (THF) and cooled in an ice bath. After adding 9.41 ml (68 mmol) of triethylamine to the solution, 3.83 ml (50 mmol) of methanesulfonyl chloride are added dropwise, keeping the temperature below 5° C. The reaction mixture is gradually warmed to room temperature, and stirred for 1 hr. The reaction mixture is poured into 200 ml of water, and extracted with ethyl acetate. The organic phase is washed with hydrochloric acid solution, water, and sodium chloride solution. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by recrystallization from toluene. 9.4 g (70%) of (4-Methylsulfonyloxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are obtained in the form of a yellow-green crystal having a melting point of 137-139° C. (dec.). 1H-NMR shows that the product is a 82:18 mixture of the E and Z isomers (two dxd signals for H-C(2 or 6) at 6.78 and 6.91 ppm.
Workup
- temperaturecooled in an ice bath
- additionare added dropwise
- customthe temperature below 5° C
- extractionextracted with ethyl acetate
- washThe organic phase is washed with hydrochloric acid solution, water, and sodium chloride solution
- dry with materialThe organic phase is dried over MgSO4
- distillationthe solvent is distilled off
- customthe residue is purified by recrystallization from toluene
Sources & evidence
- ORD record
- ord-d3822b41411a457ca102026d4824804d
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06004724
Linked notes
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