Dimethylcarbamoyl Chloride → Isouron

HRID 2052201Notes

Reaction equation

HRID 2052201 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:11][C:12]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[O:14][N:13]=1>C1(C)C=CC=CC=1.O>[CH3:1][N:2]([CH3:6])[C:3]([NH:11][C:12]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[O:14][N:13]=1)=[O:4]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 41648IsouronYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

N,N-Dimethylcarbamoyl chloride (7.91 g) and aluminum chloride (9.80 g) are added to toluene (100 ml), and the mixture is stirred at room temperature for 30 minutes. To this mixture is added 3-amino-5-t-butylisoxazole (9.81 g), and the resulting mixture is refluxed for 6 hours with stirring. After cooling, the reaction mixture is mixed with water, stirred at room temperature and shaken with toluene. The organic layer is evaporated to remove the toluene, whereby 1,1-dimethyl-3-(5-t-butyl-3-isoxazolyl)urea (14.63 g) is obtained. Yield is 98.9%. Melting point of the colorless crystalline product is 119 to 120.5° C. (after recrystallization from benzene).

Workup

  1. temperaturethe resulting mixture is refluxed for 6 hours
  2. stirringwith stirring
  3. temperatureAfter cooling
  4. stirringstirred at room temperature
  5. customThe organic layer is evaporated
  6. customto remove the toluene

Sources & evidence

ORD record
ord-bd124d54c5264ac58dc8a6d7b200d2b8
Source dataset
uspto-grants-1980_01
Patent number
US04183856

Reaction notes

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