Triethylamine → HCID 20522150, compound

HRID 223363Notes

Reaction equation

HRID 223363 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.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CCOCC>[CH2:24]([O:23][C:21]([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)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178429333HCID 178429333, compound

Product 1

HCID 20522150HCID 20522150, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.0 g (0.013 mole) 4-hydroxy-6-methyl-2-trichloromethylpyrimidine, 1.4 g (0.013 mole) triethylamine, and 75 ml ether was added 1.4 g (0.013 mole) ethyl chloroformate. The reaction mixture was refluxed for 2 hours, filtered, and rotary evaporated under aspiration to give a dark oil. This was triturated with petroleum ether and the solution decanted from tars. The solvent was stripped in vacuo and the product distilled to give 2.7 g (67% yield; bp0.5 mm 125° C.). The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. filtrationfiltered
  3. customrotary evaporated under aspiration
  4. customto give a dark oil
  5. customThis was triturated with petroleum ether
  6. customthe solution decanted from tars
  7. distillationthe product distilled
  8. customto give 2.7 g (67% yield; bp0.5 mm 125° C.)

Sources & evidence

ORD record
ord-070d05402fd847808ca5b195b38cd02e
Source dataset
uspto-grants-1982_10
Patent number
US04353908

Reaction notes

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