Pyridine → Acibenzolar Acid Impurity 21

HRID 2106947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106947
[S:1]1[C:5]2[C:6]([C:10]([NH2:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[C:10]([C:6]1[C:5]2[S:1][N:2]=[N:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)#[N:12]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 22403364Benzo-1,2,3-thiadiazole-7-carboxylic acid amide

Produkt 1

HCID 22182879Acibenzolar Acid Impurity 21

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
3 °C

Versuchsvorschrift

4.0 g (0.022 mol) of benzo-1,2,3-thiadiazol-7-ylcarboxylic acid amide are dissolved in 35 ml of tetrahydrofuran, and 3.6 ml (0.045 mol) of pyridine are added. The batch is then cooled to 3° C. and a solution of 3.9 ml (0.028 mol) of trifluoroacetic acid anhydride in 12 ml of tetrahydrofuran is added dropwise. The reaction mixture is subsequently stirred for 22 hours at room temperature and then poured onto ice/water and extracted twice with ethyl acetate. The extracts are washed with water, dried over magnesium sulfate and filtered through a layer of silica gel. Concentration by evaporation gives 3.5 g (99% of the theoretical yield) of crystalline product having a melting point of 119°-122° C.

Aufarbeitung

  1. additionpoured onto ice/water
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a layer of silica gel
  6. concentrationConcentration
  7. customby evaporation
  8. customgives 3.5 g (99% of the
  9. customtheoretical yield) of crystalline product

Quellen und Nachweise

ORD-Eintrag
ord-02dd12b840fb42fbad337f0d43ed11d7
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931581

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