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

HRID 1112574Notes

Reaction equation

HRID 1112574 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-50e467aa727c41fead393647f41125d1
Source dataset
uspto-grants-1978_10
Patent number
US04123256

Reaction notes

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