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

HRID 2097635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097635
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-5bf43f2bb757463999b3fb029e7339fc
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450351B2

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