Ethanol → Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

HRID 1274597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1274597
[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:18]([CH2:21][C:22]#N)[C:17]=3[CH:24]=2)[C:3]1=[O:25].[CH2:26]([OH:28])[CH3:27].O.S(=O)(=O)(O)[OH:31]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][C:22]([O:28][CH2:26][CH3:27])=[O:31])[C:17]=3[CH:24]=2)[C:3]1=[O:25]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 22119923HCID 22119923, Verbindung

Produkt 1

HCID 11729347Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetonitrile (1.00 g), ethanol (20.0 mL) and water (1.00 mL) is treated with concentrated sulfuric acid (10.0 mL), refluxed for 15 minutes, and poured into an ice-water mixture. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain an orange foam. Column chromatography of the foam using silica gel and a 10% ethyl acetate in methylene chloride solution gives the title product as a solid which is identified by NMR spectral analysis.

Aufarbeitung

  1. temperaturerefluxed for 15 minutes
  2. extractionThe resultant aqueous mixture is extracted with methylene chloride
  3. washThe combined organic extracts are washed sequentially with water, saturated sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an orange foam

Quellen und Nachweise

ORD-Eintrag
ord-c838f04994384bafb7373b4c6d117db6
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156700

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