Triethylamine → 5-Chloro-4-Ethoxycarbonyloxy-6-Methyl-2-Trichloromethylpyrimidine

HRID 223362Notes

Reaction equation

HRID 223362 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[N:4][C:5]([C:9]([Cl:12])([Cl:11])[Cl:10])=[N:6][C:7]=1[CH3:8].C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CCOCC>[Cl:1][C:2]1[C:3]([O:13][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:4][C:5]([C:9]([Cl:10])([Cl:11])[Cl:12])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178432777HCID 178432777, compound

Product 1

HCID 130801655-Chloro-4-Ethoxycarbonyloxy-6-Methyl-2-TrichloromethylpyrimidineYield 80.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5.8 g (0.02 mole) 5-chloro-4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 2.0 g (0.02 mole) triethylamine, and 100 ml ether was added 2.2 g (0.02 mole) ethyl chloroformate. An immediate reaction ensued and a precipitate formed. After refluxing 2 hours longer the mixture was filtered, and the filtrate was washed with aqueous potassium carbonate and then with water. Rotary evaporation yielded 5.4 g residue which was recrystallized from ligroin to give 4.6 g (69% yield) of pure product (mp 43.5°-44.5° C.). The structure was confirmed via infrared and elemental analysis.

Workup

  1. customAn immediate reaction
  2. customa precipitate formed
  3. temperatureAfter refluxing 2 hours longer the mixture
  4. filtrationwas filtered
  5. washthe filtrate was washed with aqueous potassium carbonate
  6. customRotary evaporation

Sources & evidence

ORD record
ord-e8be1a800d97415abedc3c873f699c1b
Source dataset
uspto-grants-1982_10
Patent number
US04353908

Reaction notes

Loading…