Acetone Cyanohydrin → HCID 178481848, Verbindung

HRID 870408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870408
Cl.[CH3:2][N:3]1[C:7]([OH:8])=[CH:6][CH:5]=[N:4]1.C(N(CC)CC)C.[CH3:16][N:17]1[C:22](=[O:23])[N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20](=[O:30])[C:19]([C:31](Cl)=[O:32])=[N:18]1.CC(C)(O)C#N>C(#N)C.ClCCl>[OH:8][C:7]1[N:3]([CH3:2])[N:4]=[CH:5][C:6]=1[C:31]([C:19]1[C:20](=[O:30])[N:21]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:22](=[O:23])[N:17]([CH3:16])[N:18]=1)=[O:32]

Komponenten

7

Edukt 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 866815642-Methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chlorideHCID 178478934HCID 178478934, Verbindung

Produkt 1

HCID 178481848HCID 178481848, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Next, 1.22 g (9.10 mmol) of 1-methyl-5-hydroxypyrazole hydrochloride and 1.53 g (15.17 mmol) of triethylamine were added to dichloromethane (30 ml) under ice cooling. To the mixture, the dichloromethane solution (15 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride was slowly added dropwise, and stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (30 ml), added with 0.92 g (9.10 mmol) of triethylamine and 0.05 g (0.61 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. The reaction mixture was concentrated under reduced pressure, and then the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.40 g of the target compound (yield 20%).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residues obtained
  6. temperaturerefluxed for 30 minutes
  7. temperatureunder heating
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. dissolutionthe residues were dissolved in water
  10. washwashed with ethyl acetate
  11. extractionextracted with chloroform
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe crystals obtained
  15. washwere washed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-a4cc7b759f6046f885b37a3c765bca8b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969554B2

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