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

HRID 66718

Reaction equation

HRID 66718 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.[C:20]1([N:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[C:20]1([N:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](=[O:28])[O:1][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]([Cl:12])([Cl:10])[Cl:11])[N:3]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 178429333HCID 178429333, compound

Product 1

HCID 130415296-Methyl-2-Trichloromethyl-4-Pyrimidinyl DiphenylcarbamateYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5.7 g (0.025 mole) 4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 2.6 g (0.025 mole) triethylamine, and 100 ml acetonitrile was added 5.8 g (0.025 mole) diphenylcarbamoyl chloride. The reaction mixture was refluxed 4 hours. A precipitate was filtered out and ether was added to the filtrate yielding more precipitate. Rotary evaporation gave 9.3 g residue which was recrystallized from ligroin to give 6.15 g (58% yield) of product. An analytical sample was recrystallized a second time from ligroin and had mp 132°-134° C. The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperatureThe reaction mixture was refluxed 4 hours
  2. filtrationA precipitate was filtered out and ether
  3. additionwas added to the filtrate
  4. customyielding more precipitate
  5. customRotary evaporation

Sources & evidence

ORD record
ord-b8dee56bb0454da1acd88ecf3e6eb576
Source dataset
uspto-grants-1982_08
Patent number
US04343803

Linked notes

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