Triethylamine → 6-Methyl-2-Trichloromethyl-4-Pyrimidinyl Dimethylthiocarbamate

HRID 66719Notes

Reaction equation

HRID 66719 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)=[S:23]>CCOCC>[CH3:20][N:21]([CH3:25])[C:22](=[S: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 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 178429333HCID 178429333, compound

Product 1

HCID 130415306-Methyl-2-Trichloromethyl-4-Pyrimidinyl DimethylthiocarbamateYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5.7 g (0.025 mole) 4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 2.6 g (0.025 mole) triethylamine, 3.2 g (0.025 mole) dimethylthiocarbamoyl chloride, and 100 ml ether was refluxed 16 hours. A trace of dark solid was filtered out and the solution was evaporated on a steam bath to give a solid residue. This residue was extracted with hot ligroin to yield 4.3 g (55% yield) of product (mp 81°-83° C.) on cooling. The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperaturewas refluxed 16 hours
  2. filtrationA trace of dark solid was filtered out
  3. customthe solution was evaporated on a steam bath
  4. customto give a solid residue
  5. extractionThis residue was extracted with hot ligroin

Sources & evidence

ORD record
ord-61635044421b488eb86f93ade7559371
Source dataset
uspto-grants-1982_08
Patent number
US04343803

Reaction notes

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