Water → 3-(2,5-Dichlorophenoxy)-1,1-dimethyl urea

HRID 1195603Notes

Reaction equation

HRID 1195603 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[O:4][NH2:5].[CH3:11][N:12]([CH3:16])[C:13](Cl)=[O:14].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[O:4][NH:5][C:13](=[O:14])[N:12]([CH3:16])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 135748982,5-Dichlorophenoxyamine

Product 1

HCID 137463693-(2,5-Dichlorophenoxy)-1,1-dimethyl ureaYield 61.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.00 g (28.1 mmoles) of 2,5-dichlorophenoxyamine was dissolved in 6.8 ml of pyridine, and then 3.02 g (28.1 mmoles) of dimethylcarbamoyl chloride was added. The mixture was stirred at a temperature of from 25° to 30° C. for 12 hours. After an addition of 200 ml of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and precipitated crystals were washed with hexane, whereby 4.33 g of the desired product was obtained as light yellow crystals (yield: 62%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationEthyl acetate was distilled off under reduced pressure
  5. customprecipitated crystals
  6. washwere washed with hexane

Sources & evidence

ORD record
ord-222da86cfe2049e598b5543dd9a81609
Source dataset
uspto-grants-1992_05
Patent number
US05112385

Reaction notes

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