Tesmilifene Hydrochloride → 5-Bromo-2-nitrothiophene-3-carboxamide

HRID 385713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385713
[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=[N:11]O)[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=[O:21])=CC=1.CCN(CCOC1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:11])=[O:21])[CH:3]=1

Komponenten

5

Edukt 3

HCID 175534Tesmilifene HydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 723159975-Bromo-2-nitrothiophene-3-carbaldehyde oxime

Produkt 1

HCID 534029485-Bromo-2-nitrothiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
111 °C

Versuchsvorschrift

5-Bromo-2-nitrothiophene-3-carbaldehyde oxime (45 g, 179 mmol), p-toluenesulfonic acid monohydrate (2.73 g, 14.34 mmol), dppe (1.428 g, 3.58 mmol) and Ru(PPh3)3(CO)H2 (3.29 g, 3.58 mmol) were taken up in toluene (750 mL). The flask was evacuated and back-filled with N2 (3×) before stirring at 111° C. under N2 for 24 hours. After cooling to room temperature, the reaction mixture was purified directly by flash silica gel column chromatography (0-100% EtOAc-toluene) to give the title compound as brown needles after recrystallising from EtOH-hexanes.

Aufarbeitung

  1. customThe flask was evacuated
  2. additionback-filled with N2 (3×)
  3. temperatureAfter cooling to room temperature
  4. customthe reaction mixture was purified directly by flash silica gel column chromatography (0-100% EtOAc-toluene)

Quellen und Nachweise

ORD-Eintrag
ord-4af59e4c2c164cb9bd58bc3d50117f2d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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