Dimethylcarbamoyl Chloride → HCID 12774072, compound

HRID 434611Notes

Reaction equation

HRID 434611 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[NH2:6].[OH-].[Na+].[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>C1(C)C=CC=CC=1>[F:1][C:2]([F:21])([F:22])[C:3]1[CH:4]=[C:5]([NH:6][C:27](=[O:28])[N:26]([CH3:30])[CH3:25])[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 14798Sodium HydroxideHCID 12774065HCID 12774065, compound

Product 1

HCID 12774072HCID 12774072, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Trifluoromethyl-4-(2-naphthyloxy)aniline (9.1 g) was dissolved in 200 ml of toluene, and 30 ml of 40% aqueous sodium hydroxide solution and 6.5 g of N,N-dimethylcarbamyl chloride were added thereto. The reaction mixture was heated under reflux for 10 hours and then cooled to room temperature. The toluene layer was washed with water, the solvent was removed by distillation under reduced pressure and the residue was rerecrystallized from ethanol to obtain 5.1 g of N'-[3-trifluoromethyl-4-(2-naphthyloxy)phenyl]-N,N-dimethylurea as white needles. M.P. 210°-211° 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 by distillation under reduced pressure

Sources & evidence

ORD record
ord-8b7022e140274a40afff8c444a94baa8
Source dataset
uspto-grants-1983_08
Patent number
US04399072

Reaction notes

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