Water → (5-Methylsulfonyloxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile

HRID 612358

Reaktionsgleichung

Reaktionsgleichung von HRID 612358
[OH:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])[CH:5]=[CH:4]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C1COCC1>[CH3:24][S:25]([O:1][N:2]=[C:3]1[S:7][C:6](=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])[CH:5]=[CH:4]1)(=[O:27])=[O:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59115159(5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile

Produkt 1

HCID 54441994(5-Methylsulfonyloxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrileAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5 g (22 mmol) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile are dissolved in 50 ml of THF and cooled in an ice bath. After adding 4.6 ml (33 mmol) of triethylamine to the solution, 1.9 ml (24 mmol) of methanesulfonyl chloride are added dropwise, keeping the temperature below 5° C. The reaction mixture is stirred while cooling in an ice bath for 30 min. The reaction mixture is poured into 200 ml of water, and extracted with ethyl acetate. The organic phase is washed with hydrochloric acid solution 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. 5.2 g (77%) of (5-Methylsulfonyloxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile are obtained in the form of greenish brown crystals having a melting point of 160-162° C. (dec.).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionare added dropwise
  3. customthe temperature below 5° C
  4. temperaturewhile cooling in an ice bath for 30 min
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with hydrochloric acid solution and sodium chloride solution
  7. dry with materialThe organic phase is dried over MgSO4
  8. distillationthe solvent is distilled off
  9. customthe residue is purified by recrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-607654a676584d24bb1028defa5a2427
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06004724

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