Boron trifluoride etherate → 3-[3-(1,3-Dithiolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49009

Reaktionsgleichung

Reaktionsgleichung von HRID 49009
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=C(C=O)[C:17]=3[CH:23]=2)[C:3]1=[O:24].[CH:25]([SH:28])([SH:27])[CH3:26].B(F)(F)F.[CH3:33][CH2:34]OCC>C(Cl)Cl>[S:27]1[CH2:34][CH2:33][S:28][CH:25]1[C:26]1[C:17]2[CH:23]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:9])([F:11])[F:10])[N:2]([CH3:1])[C:3]3=[O:24])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 336451,1-EthanedithiolHCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Produkt 1

HCID 206342033-[3-(1,3-Dithiolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracilAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (0.300 g, 0.850 mmol) and methylene chloride is added ethanedithiol (0.0940 g, 1.00 mmol) and boron trifluoride-etherate (0.200 ml). The resultant mixture is stirred overnight at room temperature and partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to a yellow solid which is stirred in hot methylcyclohexane and filtered to afford the title compound as a light yellow solid (0.170 g, 46.3%, mp 227-232° C.) which is identified by NMR spectral analysis.

Aufarbeitung

  1. custompartitioned between methylene chloride and saturated sodium bicarbonate
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo to a yellow solid which
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8bf089df8a384e13a27e826f43e36cc3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706663B2

Verknüpfte Notizen

Wird geladen…