Pyridine → N'-[4-(4-tert-butylphenethyloxy)phenyl]-N-methoxy-N-methylurea

HRID 65821

Reaction equation

HRID 65821 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][C:8]([CH2:9][CH2:10][O:11][C:12]2[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][N:23]([CH3:27])[C:24](Cl)=[O:25].N1C=CC=CC=1.[Cl-].[NH+]1C=CC=CC=1>O.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:20]=[CH:19][C:8]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([NH:16][C:24](=[O:25])[N:23]([O:22][CH3:21])[CH3:27])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 69401Einecs 211-027-4HCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 227560014-(4-Tert-butylphenethyloxy)aniline

Product 1

HCID 22756005N'-[4-(4-tert-butylphenethyloxy)phenyl]-N-methoxy-N-methylureaYield 26.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 26.9 g of 4-(4-tert-butylphenethyloxy)aniline, 13 g of N-methoxy-N-methylcarbamyl chloride, 10 ml of pyridine and 300 ml of toluene is heated under reflux for 7 hours. Thereafter, water is added to dissolve pyridinium chloride, and the separated toluene layer is washed with dilute hydrochloric acid, thoroughly washed with water and dried over anhydrous sodium sulfate. The solvent is then removed under reduced pressure, and the crude crystals obtained are repeatedly recrystallized from ethanol to obtain 9.3 g of N'-[4-(4-tert-butylphenethyloxy)phenyl]-N-methoxy-N-methylurea as white needles, M.P. 14°-15° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 7 hours
  3. washthe separated toluene layer is washed with dilute hydrochloric acid
  4. washthoroughly washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is then removed under reduced pressure
  7. customthe crude crystals obtained
  8. customare repeatedly recrystallized from ethanol

Sources & evidence

ORD record
ord-af08b02af2aa4bca8204bcf5fa2b9ff0
Source dataset
uspto-grants-1978_12
Patent number
US04129436

Linked notes

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