Chloromethyl Methyl Ether → alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

HRID 1577464

Reaktionsgleichung

Reaktionsgleichung von HRID 1577464
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][CH3:15])=[O:4].Cl[CH2:17][O:18][CH3:19].[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:5]([CH2:17][O:18][CH3:19])[C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][CH3:15])=[O:4]

Komponenten

6

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 20570575alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide

Produkt 1

HCID 20554723alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 165294Benzyltriethylammonium bromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture containing alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide (11.0 g; 0.048 mole), 10 ml. of (chloromethyl)methyl ether and 3.0 g. of benzyltriethylammonium bromide in 100 ml. of methylene chloride was added 50 ml. of a 50% sodium hydroxide solution. The temperature of the reaction mixture increased to 40° C. The reaction mixture was stirred for 1 hour after which time the layers were separated, and the organic methylene chloride layer was concentrated in vacuo yielding a white solid. The white solid was recrystallized from isopropanol to yield alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (11.8 g; 90% yield) as a white solid having a melting point of 104°-106° C. and the following analysis:

Aufarbeitung

  1. customwere separated
  2. concentrationthe organic methylene chloride layer was concentrated in vacuo
  3. customyielding a white solid
  4. customThe white solid was recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-eaf4e6cbbedc4da29f6bd74118158f34
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04288242

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