تفاعل #746929

معادلة التفاعل

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

المردود 71.0%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to 0° C
2. 2
   workup.WAITAfter 30 min.
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   ترشيحfiltered
7. 7
   أخرىAfter removal of solvent the residue
8. 8
   أخرىchromatographed (CH2Cl2/Ethanol:99/1)

الإجراء التجريبي

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.

المصدر