Reaktion #746929

Reaktionsgleichung

N-(5-Amino-2-methyl-phenyl)-acetamide

NaH

2-chloro-oxazole-5-carboxylic acid methyl ester

→

2-(5-Amino-2-methyl-phenylamino)-oxazole-5-carboxylic acid methyl ester

Ausbeute 71.0%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 0° C
2. 2
   workup.WAITAfter 30 min.
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   SonstigeAfter removal of solvent the residue
8. 8
   Sonstigechromatographed (CH2Cl2/Ethanol:99/1)

Vorschrift

A solution of N-(5-Amino-2-methyl-phenyl)-acetamide (0.51 g, 3.1 mmol) in THF (12 mL) was added to a suspension of NaH (186 mg, 4.65 mmol, 60% dispersion in mineral oil) in THF (12 mL) at 0° C. under an atmosphere of argon. The mixture was stirred for 30 min. at room temperature and cooled to 0° C. A solution of 2-chloro-oxazole-5-carboxylic acid methyl ester (0.5 g, 3.1 mmol) in THF (12 mL) was added dropwise to the mixture. After 30 min., at 0° C., the reaction was poured into ice water (30 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and filtered. After removal of solvent the residue was silica gel column chromatographed (CH2Cl2/Ethanol:99/1) to give 0.54 g of 2-(5-Amino-2-methyl-phenylamino)-oxazole-5-carboxylic acid methyl ester (71%) as a Colorless syrup.

Quelle