2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → 3-(6-Fluoro-3-methyl-1,2-benzisoxazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 277363

Reaktionsgleichung

Reaktionsgleichung von HRID 277363
[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.CN(C)[C:15]1[O:16][C:17](=[O:25])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=1>C(O)(=O)C>[F:12][C:3]1[C:2]([N:1]2[C:17](=[O:25])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[NH:20][C:15]2=[O:16])=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][O:9][C:5]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 183144706-Fluoro-3-methylbenzo[d]isoxazol-5-amine

Produkt 1

HCID 183145023-(6-Fluoro-3-methyl-1,2-benzisoxazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-6-fluoro-3-methyl-1,2-benzisoxazole (4.85 g, 0.029 mol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (6.70 g, 0.0320 mol) in acetic acid is refluxed for 90 minutes, cooled to room temperature, and poured into an ice-water mixture. The resultant aqueous mixture is filtered to obtain a solid. The solid is air-dried and dissolved in ethyl acetate. The resultant organic solution is washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow solid (7.00 g, mp 235-237° C.) which is identified by NMR spectral analyses.

Aufarbeitung

  1. temperatureis refluxed for 90 minutes
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. customThe solid is air-dried
  5. dissolutiondissolved in ethyl acetate
  6. washThe resultant organic solution is washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4ce46596b9ed4e759054c3cee9135dc7
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355796B1

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