Bromine → Methyl 5-formyl-1,2,3-thiadiazole-4-carboxylate

HRID 1845764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845764
C[O:2][CH2:3][C:4]1[S:8][N:7]=[N:6][C:5]=1[C:9]([O:11][CH3:12])=[O:10].BrBr>C(Cl)(Cl)(Cl)Cl>[CH:3]([C:4]1[S:8][N:7]=[N:6][C:5]=1[C:9]([O:11][CH3:12])=[O:10])=[O:2]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 2825090HCID 2825090, Verbindung

Produkt 1

HCID 14913987Methyl 5-formyl-1,2,3-thiadiazole-4-carboxylateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Methyl 5-(methoxymethyl)-1,2,3-thiadiazole-4-carboxylate (4.18 g, 0.022 mol) was dissolved in carbon tetrachloride (60 mL). To the solution was added bromine (4.18 g, 0.026 mol) and the solution was refluxed upon irradiation with long wavelength UV light (100 watts) for 3 h. The volatiles were evaporated in vacuo and the crude material purified by flash chromatography to give the desired product (2.70 g, 71%) as a viscous oil. 1H NMR (400 MHz, CDCl3): δ□ 10.67 (s, 1H), 4.15 (s, 3H). MF=C5H4N2O3S; LCMS calculated for C5H5N2O3S (M+H)+: m/z=173.0.

Aufarbeitung

  1. temperaturethe solution was refluxed upon irradiation with long wavelength UV light (100 watts) for 3 h
  2. customThe volatiles were evaporated in vacuo
  3. customthe crude material purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d13f68d1b1f45a5a32898309e525e97
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08951536B2

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