1,4-Dioxane--water (1/1) → 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

HRID 49003

Reaktionsgleichung

Reaktionsgleichung von HRID 49003
Br[CH:2](Br)[C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.[O:26]1CCOCC1.O>[N+]([O-])([O-])=O.[Ag+].C(Cl)Cl>[CH3:23][N:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][C:17](=[O:18])[N:12]([C:9]2[CH:10]=[CH:11][C:6]3[S:5][N:4]=[C:3]([CH:2]=[O:26])[C:7]=3[CH:8]=2)[C:13]1=[O:24]

Komponenten

5

Edukt 2

HCID 218864351,4-Dioxane--water (1/1)HCID 221198393-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Produkt 1

HCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.500 g, 0.00100 mol) in a dioxane/water mixture (5:2) is treated with silver nitrate (0.340 g, 0.00200 mol), refluxed for 90 minutes, cooled to room temperature, stirred for 18 hrs, refluxed for three hrs, cooled, and filtered through a pad of diatomaceous earth. The resultant filtrate is concentrated in vacuo to obtain an aqueous mixture. The aqueous mixture is extracted with methylene chloride. The organic extract is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Column chromatography of the solid using silica gel and methylene chloride gives the title product as a solid (0.240 g, mp 193-194.5° C.).

Aufarbeitung

  1. temperaturerefluxed for 90 minutes
  2. temperaturerefluxed for three hrs
  3. temperaturecooled
  4. filtrationfiltered through a pad of diatomaceous earth
  5. concentrationThe resultant filtrate is concentrated in vacuo
  6. customto obtain an aqueous mixture
  7. extractionThe aqueous mixture is extracted with methylene chloride
  8. extractionThe organic extract
  9. washis washed sequentially with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customto obtain a solid

Quellen und Nachweise

ORD-Eintrag
ord-6b3cd572d4d840a59b547b957ebf8cee
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706663B2

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