تفاعل #2558

معادلة التفاعل

3-methoxy-N-(2-methoxyphenyl) benzamide

sodium hydride

2-tetrahydropyranyloxyethyl bromide

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title compound

المردود 67.0%

N-(2-Tetrahydropyranyloxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide

المردود 67.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىat room temperature
2. 2
   workup.STIRRINGAfter additional 5 minutes of stirring under an ultrasonic irradiation condition at the same temperature
3. 3
   workup.STIRRINGAfter 1 hour of stirring at room temperature
4. 4
   workup.STIRRINGsubsequent stirring at 70° C. for 6 hours
5. 5
   أخرىDMF was removed by evaporation
6. 6
   workup.ADDITIONthe resulting residue was mixed with water (20 ml)
7. 7
   استخلاصextracted with ether
8. 8
   غسيلwashed with water and saturated brine
9. 9
   تجفيفThe resulting organic layer was dried on anhydrous magnesium sulfate
10. 10
    أخرىthe solvent was removed by evaporation
11. 11
    أخرىthe resulting orange oily residue was purified

الإجراء التجريبي

In an atmosphere of argon, 3-methoxy-N-(2-methoxyphenyl) benzamide (500 mg, 1.94 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (85 mg, 60%, 2.13 mmol) at room temperature, followed by 20 minutes of stirring. After additional 5 minutes of stirring under an ultrasonic irradiation condition at the same temperature, to this was added 2-tetrahydropyranyloxyethyl bromide (446 mg, 2.13 mmol) at room temperature. After 1 hour of stirring at room temperature and subsequent stirring at 70° C. for 6 hours, DMF was removed by evaporation, and the resulting residue was mixed with water (20 ml), extracted with ether and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting orange oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=2:1) to obtain 501 mg (67.0%) of the title compound in the form of yellow oil.

المصدر