Tributylamine → 1,2-Benzisothiazole, 3-chloro-5-nitro-

HRID 277375

Reaktionsgleichung

Reaktionsgleichung von HRID 277375
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][NH:10][C:9](=O)[C:8]=2[CH:13]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[Cl:16][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[S:11][N:10]=1

Komponenten

5

Edukt 3

HCID 7622TributylamineHCID 24813Phosphorus oxychlorideHCID 131869501,2-Benzisothiazol-3(2H)-one, 5-nitro-

Produkt 1

HCID 1980981,2-Benzisothiazole, 3-chloro-5-nitro-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
109 °C

Versuchsvorschrift

A mixture of 5-nitro-1,2-benzisothiazol-3(2H)-one (10.0 g, 0.0510 mol), phosphorus oxychloride (40.0 mL, 0.429 mol) and tributylamine (12.0 mL, 0.050 mol) is heated at 103-115° C. for six hours, stirred at room temperature overnight, 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 and saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a gum. Column chromatography of the gum using silica gel and methylene chloride gives the title product as an orange-yellow solid which is identified by NMR spectral analysis.

Aufarbeitung

  1. extractionThe resultant aqueous mixture is extracted with methylene chloride
  2. washThe combined organic extracts are washed sequentially with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a gum

Quellen und Nachweise

ORD-Eintrag
ord-b97e097d6d624ba4aaf28e75807e741e
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355796B1

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