Sodium Bicarbonate → 2-Aminobenzo[b]thiophene-3-carboxamide

HRID 1594235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594235
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]#[N:12].C([O-])(O)=[O:14].[Na+]>OS(O)(=O)=O>[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([NH2:12])=[O:14]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 232735812-Amino-1-benzothiophene-3-carbonitrile

Produkt 1

HCID 122835332-Aminobenzo[b]thiophene-3-carboxamideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 2-amino-benzo[b]thiophene-3-carbonitrile (50 mg, 0.29 mmol) in concentrated H2SO4 (1.5 mL) was heated at 60° C. for 2 h. The solution was poured into ice-water (5 mL), mixed with saturated NaHCO3 solution (30 mL), and extracted with ethyl acetate (30 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 1:1) then provided the title compound (23 mg, 41%) as a white solid: MS (ES) m/z 193 (M+H)+.

Aufarbeitung

  1. extractionextracted with ethyl acetate (30 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9b99027e004f4945b7501a9a92c1a02e
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300952B2

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