반응 #7182

반응 방정식

potassium carbonate

2-aminothiophenol

chloroacetic acid

→

2-chloromethylbenzoxazole

2-chloromethylbenzothiazole

용매

water

—

polyphosphoric acid

반응 조건

후처리

1. 1
   온도The reaction was then cooled
2. 2
   추출The mixture was then extracted with ethyl acetate
3. 3
   건조the combined organic fractions were then dried over MgSO4
4. 4
   농축concentrated
5. 5
   기타The residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes)

실험 절차

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).

출처