Chloromethyl ethyl ether → alpha-chloro-N-(ethoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

HRID 1577465

Reaktionsgleichung

Reaktionsgleichung von HRID 1577465
[H-].[K+].[Cl:3][CH2:4][C:5]([NH:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[O:16][CH3:17])=[O:6].[H][H].Cl[CH2:21][O:22][CH2:23][CH3:24].C(=O)(O)[O-].[Na+]>CCCCC.C(OCC)C.O1CCCC1>[Cl:3][CH2:4][C:5]([N:7]([CH2:21][O:22][CH2:23][CH3:24])[C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[O:16][CH3:17])=[O:6]

Komponenten

9

Edukt 5

HCID 18523Chloromethyl ethyl etherHCID 82127Potassium hydrideHCID 516892Sodium BicarbonateHCID 20570575alpha-chloro-N-(2,6-dimethoxyphenyl)acetamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 20570574alpha-chloro-N-(ethoxymethyl)-N-(2,6-dimethoxyphenyl)acetamideAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8003PentaneLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a mixture containing potassium hydride (2.2 g; 0.055 mole) in 50 ml. of tetrahydrofuran was added a solution of alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide (11.5 g; 0.05 mole) in 250 ml. of tetrahydrofuran. Hydrogen gas evolved from the reaction mixture. To the reaction mixture was added an excess of (chloromethyl)ethyl ether (10 ml.) which caused the temperature of the reaction mixture to increase to 45° C. An excess of a sodium bicarbonate solution (100 ml.) was then added to the reaction mixture followed by the addition of 100 ml. of diethyl ether. The layers were separated and the organic ether layer was dried over magnesium sulfate, filtered and concentrated in vacuo to yield an amber oil. The amber oil was separated on a silica gel column using a 3:2 hexane:diethyl ether mixture as the eluant. Fractions containing a crude product were combined and concentrated in vacuo to yield a solid residue. The solid residue was taken up in pentane and the pentane solution was scratched until a white solid formed. The pentane solution containing the white solid was filtered and the white solid was recrystallized from heptane to yield alpha-chloro-N-(ethoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (3.0 g; 20.9% yield) having a melting point of 95°-97° C. and the following analysis:

Aufarbeitung

  1. additionfollowed by the addition of 100 ml
  2. customThe layers were separated
  3. dry with materialthe organic ether layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield an amber oil
  7. customThe amber oil was separated on a silica gel column
  8. additionFractions containing a crude product
  9. concentrationconcentrated in vacuo
  10. customto yield a solid residue
  11. customformed
  12. filtrationwas filtered
  13. customthe white solid was recrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-6f05337b05f14ec4849de206835268c2
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04288242

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