Hydrochloric Acid → [(5-Nitro-1,2-benzisothiazol-3-yl)oxy]acetonitrile

HRID 428403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428403
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][NH:10][C:9](=[O:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]#[N:23].Cl>CN(C)C=O.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([O:12][CH2:21][C:22]#[N:23])[C:8]=2[CH:13]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 131869501,2-Benzisothiazol-3(2H)-one, 5-nitro-

Produkt 1

HCID 18314467[(5-Nitro-1,2-benzisothiazol-3-yl)oxy]acetonitrileAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-nitro-1,2-benzisothiazol-3(2H)-one (17.5 g, 89.2 mmol) in N,N-dimethylformamide is treated with potassium carbonate (18.5 g, 134 mmol), stirred at room temperature for 30 minutes, treated with bromoacetonitrile (16.0 g, 133 mmol), stirred at room temperature overnight, and poured onto ice. The resultant aqueous mixture is acidified to pH 3 with hydrochloric acid and extracted with ethyl acetate. The combined organic extracts are 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 yellow solid (15.0 g, mp 123-124.5° C.).

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. additionpoured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a solid

Quellen und Nachweise

ORD-Eintrag
ord-71418c1d64684966ab5e675cd59e7d69
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313295B1

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