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Sodium hydride → 3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide

HRID 2462
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2462
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])=[O:7].[H-].[Na+].[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH2:29][CH2:30]Br>CN(C=O)C>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:28][CH2:29][CH2:30][N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[C:6](=[O:7])[C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([O:2][CH3:1])[CH:4]=1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 9028663-methoxy-N-(2-methoxyphenyl)benzamide

Produkt 1

HCID 539260843-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customat room temperature
  2. stirringAfter additional 5 minutes of stirring under an ultrasonic irradiation condition at the same temperature
  3. stirringAfter 1 hour of stirring at room temperature
  4. stirringsubsequent stirring at 70° C. for 6 hours
  5. customDMF was removed by evaporation
  6. additionthe resulting residue was mixed with water (20 ml)
  7. extractionextracted with ether
  8. washwashed with water and saturated brine
  9. dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
  10. customthe solvent was removed by evaporation
  11. customthe resulting orange oily residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-3ded3b8d2ed540a4b76f3f398d06c312
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728835

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