Dimethylcarbamoyl Chloride → 6-Methyl-2-trichloromethyl-4-pyrimidinyl dimethylcarbamate

HRID 66717Notes

Reaction equation

HRID 66717 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(N(CC)CC)C.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23]>C(#N)C>[CH3:20][N:21]([CH3:25])[C:22](=[O:23])[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

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178429333HCID 178429333, compound

Product 1

HCID 130415286-Methyl-2-trichloromethyl-4-pyrimidinyl dimethylcarbamateYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.7 g (0.025 mole) 4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 5.1 g (0.05 mole) triethylamine, and 100 ml acetonitrile was stirred and 5.4 g (0.05 mole) dimethylcarbamoyl chloride was added to the mixture. The reaction mixture was stirred 2 hours under reflux, and allowed to cool. A solid was filtered out after cooling and washed with water to give 3.6 g (48% yield; mp 83.5°-84.5° C.). The structure was confirmed via infrared and elemental analysis.

Workup

  1. stirringThe reaction mixture was stirred 2 hours
  2. temperatureunder reflux
  3. temperatureto cool
  4. filtrationA solid was filtered out
  5. temperatureafter cooling
  6. washwashed with water
  7. customto give 3.6 g (48% yield; mp 83.5°-84.5° C.)

Sources & evidence

ORD record
ord-edb09a750cee4f589a429a93eeee7555
Source dataset
uspto-grants-1982_08
Patent number
US04343803

Reaction notes

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