Water → 2-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid ethyl ester

HRID 899388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899388
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)[CH3:2].[N:13]1[S:14][N:15]=[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=12.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:22][C:20]1[CH:19]=[CH:18][C:17]2=[N:13][S:14][N:15]=[C:16]2[CH:21]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27718862,1,3-Benzothiadiazol-5-olHCID 2796614Ethyl chloronicotinate

Produkt 1

HCID 235293462-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid ethyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-nicotinic acid ethyl ester (0.516 g, 3 mmol), benzo-[2,1,3]-thiadiazol-5-ol (0.46 g, 3 mmol), and cesium carbonate (2.07 g, 6.3 mmol) was stirred in 40 ml N,N-dimethylformamide at 80° C. for 48 h. The dark orange mixture was cooled and poured into water (600 ml) and extracted with ethyl acetate. The combined organic layers were washed with water and brine, and dried over (Na2SO4). The mixture was concentrated in vacuo to give 0.74 g of a yellow solid (82% yield).

Aufarbeitung

  1. temperatureThe dark orange mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over (Na2SO4)
  5. concentrationThe mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7b5b9ef9a334a48824fbad0b799446b
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354941B2

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