Dimethylcarbamoyl Chloride → N'-[4-(2-naphthyloxy)phenyl]-N,N-dimethylurea

HRID 434608Notes

Reaction equation

HRID 434608 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.[OH-].[Na+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:23](=[O:24])[N:22]([CH3:26])[CH3:21])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 14798Sodium HydroxideHCID 35808292-(4-Aminophenoxy)naphthalene

Product 1

HCID 12774071N'-[4-(2-naphthyloxy)phenyl]-N,N-dimethylureaYield 55.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Twenty-five grams of 4-(2-naphthyloxy)aniline were dissolved in 200 ml of toluene, and 100 ml of 40% aqueous sodium hydroxide solution and 12 g of N,N-dimethylcarbamyl chloride were added thereto. The reaction mixture was heated under reflux for 10 hours, and its temperature was cooled to room temperature. The toluene layer was washed with water, and the solvent was removed under reduced pressure. The residue was recrystallized from ethanol to obtain 18 g of N'-[4-(2-naphthyloxy)phenyl]-N,N-dimethylurea as white needles. M.P., 156°-157° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 10 hours
  3. washThe toluene layer was washed with water
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c958c826912b4a75a6fb9432049183ba
Source dataset
uspto-grants-1983_08
Patent number
US04399072

Reaction notes

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