Formamide → 5-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

HRID 1914569

Reaktionsgleichung

Reaktionsgleichung von HRID 1914569
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=O)[CH2:11]Br)[S:7][CH:6]=1)=[O:4].[CH:14]([NH2:16])=[O:15]>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:16]=[CH:14][O:15][CH:11]=2)[S:7][CH:6]=1)=[O:4]

Komponenten

3

Edukt 2

HCID 713FormamideHCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

Produkt 1

HCID 581102445-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.4 g, 1.52 mmol) was dissolved in formamide (2 mL) and the tube purged with nitrogen and then sealed. The mixture was heated at 170° C. for 20 minutes. The resultant solution was diluted with HCl (1 M) and water and washed with ethyl acetate. The organic phase was evaporated then purified by chromatography on a silica II cartridge, eluting with 2:1 pentane:DCM to neat DCM, to give the side product, 5-oxazol-4-yl-thiophene-3-carboxylic acid methyl ester as white solid (0.049 g). LCMS m/z 251.35 [M+MeCN+H]+ R. T.=3.07 min (Analytical Method 6).

Aufarbeitung

  1. customthe tube purged with nitrogen
  2. customsealed
  3. additionThe resultant solution was diluted with HCl (1 M) and water
  4. washwashed with ethyl acetate
  5. customThe organic phase was evaporated
  6. customthen purified by chromatography on a silica II cartridge
  7. washeluting with 2:1 pentane

Quellen und Nachweise

ORD-Eintrag
ord-b807fab4938e4987a356bb06be0a6677
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614209B2

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