تفاعل #40262

معادلة التفاعل

2-chloro-1-methylpyridinium iodide

(1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid

triethylamine

2-iodo-6-methoxyaniline

→

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide

المردود 89.6%

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxyphenyl)acetamide

المردود 89.6%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture is heated
2. 2
   درجة الحرارةat reflux for 20 hours
3. 3
   درجة الحرارةAfter cooling
4. 4
   استخلاصacidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane
5. 5
   غسيلThe organic phases are washed with saturated aqueous sodium chloride solution
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   أخرىevaporated under vacuum
8. 8
   أخرىPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)

الإجراء التجريبي

A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%).

المصدر