2-(Chloromethyl)anisole → N-[4-(2-methoxybenzyloxy)-phenyl]-N'-methyl-N'-methoxyurea

HRID 1112574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1112574
[O-]CC.[Na+].[Na].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]([CH3:19])[O:17][CH3:18])=[O:15])=[CH:9][CH:8]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Cl>CN(C)C=O.O.C(O)C>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]([CH3:19])[O:17][CH3:18])=[O:15])=[CH:9][CH:8]=1

Komponenten

8

Edukt 4

HCID 814952-(Chloromethyl)anisoleHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13254818N'-(4-Hydroxyphenyl)-N-methoxy-N-methylurea

Produkt 1

HCID 12893515N-[4-(2-methoxybenzyloxy)-phenyl]-N'-methyl-N'-methoxyurea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To an ethanolic solution of sodium ethoxide prepared from ethanol (200 ml) and sodium (2.5 g), N-(4-hydroxyphenyl)-N'-methyl-N'-methoxyurea (20 g) is added, and a solution of 2-methoxybenzyl chloride (17 g) in N,N-dimethylformamide (50 ml) is added dropwise thereto. The reaction mixture is gradually heated, kept under reflux for 3 hours and cooled to room temperature. The reaction mixture is poured onto cold water (1 liter). The precipitated crystals are collected by filtration, washed with water, dried and recrystallized from ethanol to give N-[4-(2-methoxybenzyloxy)-phenyl]-N'-methyl-N'-methoxyurea (Compound No. 23) (12 g) as white scales. M.P., 98° C.

Aufarbeitung

  1. additionis added
  2. temperatureThe reaction mixture is gradually heated
  3. temperatureunder reflux for 3 hours
  4. filtrationThe precipitated crystals are collected by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-50e467aa727c41fead393647f41125d1
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04123256

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