Carbon Dioxide → 1,3-Benzothiazol-6-ylacetonitrile

HRID 607578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 607578
[C-:1]#[N:2].[K+].C(O)CO.O.C(=O)=O.[S:12]1[C:16]2[CH:17]=[C:18]([CH2:21]O)[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1>O.CN(C=O)C>[S:12]1[C:16]2[CH:17]=[C:18]([CH2:21][C:1]#[N:2])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 9032Potassium CyanideHCID 178603856-(Hydroxymethyl)benzothiazoleHCID 20437942Ethylene glycol water

Produkt 1

HCID 592163101,3-Benzothiazol-6-ylacetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of potassium cyanide (0.68 g, 0.010 mol) in water (3.0 mL) was added under nitrogen to a cooled (with an ethylene glycol/water (4/1)/dry ice bath) solution of 1,3-benzothiazol-6-ylmethanol in DMF (30 mL). The reaction mixture was warmed to 0° C., and stirred for 30 min. Water was added and the reaction mixture was extracted with DCM. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was flash chromatographed on a silica gel column with ethyl acetate in hexane from 10-30% to afford the desired product (1.07 g). Analytical LCMS: (M+H)+=175.2.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a silica gel column with ethyl acetate in hexane from 10-30%

Quellen und Nachweise

ORD-Eintrag
ord-24a54df5c89f489abbbf635b3c8c34fa
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915408B2

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