Acetone → 6-Methyl-2-Trichloromethyl-4-Pyrimidinyl Diethylcarbamate

HRID 66724Notes

Reaction equation

HRID 66724 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]([Cl:12])([Cl:11])[Cl:10])[N:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].[CH3:19][N:20](C)[C:21](Cl)=[O:22].C[C:26]([CH3:28])=O>>[CH2:19]([N:20]([CH2:26][CH3:28])[C:21](=[O:22])[O:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]([Cl:12])([Cl:10])[Cl:11])[N:3]=1)[CH3:13]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 178429333HCID 178429333, compound

Product 1

HCID 130415326-Methyl-2-Trichloromethyl-4-Pyrimidinyl Diethylcarbamate

Procedure

A mixture of 5.8 g (0.027 mole) 4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 3.3 g (0.024 mole) potassium carbonate, 3.3 g (0.024 mole) dimethylcarbamoyl chloride, and 100 ml acetone was refluxed 5 hours. A precipitate was filtered out and the filtrate rotary evaporated to give 10.2 g residue. This was taken up in chloroform, the solution washed with 1% sodium hydroxide, water, and dried over anhydrous magnesium sulfate. Rotary evaporation yielded 5.2 g residue which was recrystallized from petroleum ether to give 2.1 g (24% yield) of product. An analytical sample recrystallized a second time from petroleum ether had mp 77°-77.5° C. The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperaturewas refluxed 5 hours
  2. filtrationA precipitate was filtered out
  3. customthe filtrate rotary evaporated

Sources & evidence

ORD record
ord-e649a692c4fb41879d7c7deb50b8f5d0
Source dataset
uspto-grants-1982_08
Patent number
US04343803

Reaction notes

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