Acetone Cyanohydrin → HCID 178463114, Verbindung

HRID 1857320

Reaktionsgleichung

Reaktionsgleichung von HRID 1857320
Cl.[CH2:2]([N:4]1[C:8]([OH:9])=[CH:7][CH:6]=[N:5]1)[CH3:3].C(N(CC)CC)C.[O:17]1[CH2:21][CH2:20][C:19]([C:22]2[C:23]([CH3:35])=[C:24]([CH:28]=[CH:29][C:30]=2[S:31]([CH3:34])(=[O:33])=[O:32])[C:25](Cl)=[O:26])=[N:18]1.CC(C)(O)C#N>C(Cl)(Cl)Cl>[O:17]1[CH2:21][CH2:20][C:19]([C:22]2[C:23]([CH3:35])=[C:24]([CH:28]=[CH:29][C:30]=2[S:31]([CH3:34])(=[O:33])=[O:32])[C:25]([C:7]2[CH:6]=[N:5][N:4]([CH2:2][CH3:3])[C:8]=2[OH:9])=[O:26])=[N:18]1

Komponenten

6

Edukt 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 112550833-(4,5-Dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chlorideHCID 178463041HCID 178463041, Verbindung

Produkt 1

HCID 178463114HCID 178463114, VerbindungAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To 2.75 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid were added 30 ml of benzene, then 1.7 ml of thionyl chloride and a drop of pyridine to heat at reflux for 3 hours. The reaction solution was cooled down. The solvent was distilled out under reduced pressure to give 2.90 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride. Separately 0.93 g of 1-ethyl-5-hydroxypyrazole hydrochloride was dissolved in 20 ml of chloroform, and 1.60 g of triethylamine was added, while cooling with ice. Into the obtained solution was added dropwise 10 ml of a chloroform solution containing 1.90 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride to stir at room temperature for 30 minutes, and 0.76 g of triethylamine and 0.16 g of acetone cyanohydrin were added to further stir overnight. The reaction solution was washed with dilute hydrochloric acid, then with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure. Methanol was added to the residue. The obtained crystals were separated by filtration to give 1.59 g of the title compound as white crystals. m.p. 183~184.5° C.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. washThe reaction solution was washed with dilute hydrochloric acid
  3. dry with materialwith a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure
  5. additionMethanol was added to the residue
  6. customThe obtained crystals were separated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5dfc44ea4ec545fa92afe03413a59bb1
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147031

Verknüpfte Notizen

Wird geladen…