تفاعل #7182

معادلة التفاعل

potassium carbonate

2-aminothiophenol

chloroacetic acid

→

2-chloromethylbenzoxazole

2-chloromethylbenzothiazole

المذيبات

water

—

polyphosphoric acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was then cooled
2. 2
   استخلاصThe mixture was then extracted with ethyl acetate
3. 3
   تجفيفthe combined organic fractions were then dried over MgSO4
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes)

الإجراء التجريبي

Using literature procedures (Addison, A. W.; Nageswara Rao, T.; Wahlgren, C. G. J. Heterocyclic Chem. 1983, 20, 1481–1484) a substituted 2-aminophenol (or a 2-aminothiophenol (5 mmol)) was mixed with chloroacetic acid (940 mg, 10 mmol) in polyphosphoric acid (5 mL), and the viscous mixture was then heated to 120° C. for 3 hours. The reaction was then cooled, and diluted with water (˜20 mL) and then neutralized with potassium carbonate to pH˜7. The mixture was then extracted with ethyl acetate, and the combined organic fractions were then dried over MgSO4 and concentrated. The residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes) to afford the desired 2-chloromethylbenzoxazole (or 2-chloromethylbenzothiazole).

المصدر