Diethyl Ether → HCID 13080167, compound

HRID 223364Notes

Reaction equation

HRID 223364 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.CCOCC.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>C1C=CC=CC=1>[CH:29]([O:28][C:26]([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:27])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 178429333HCID 178429333, compound

Product 1

HCID 13080167HCID 13080167, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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 1.6 g (0.013 mole) isopropyl chloroformate. The reaction mixture was refluxed one hour, filtered, and rotary evaporated to give a yellow oil. The oil was distilled (bp1.2 mm 120° C.) to give a cloudy yellow oil. This was taken up in benzene, filtered, and the solvent removed leaving 2.4 g (57% yield) of product. The structure was confirmed via infrared and elemental analysis.

Workup

  1. temperatureThe reaction mixture was refluxed one hour
  2. filtrationfiltered
  3. customrotary evaporated
  4. customto give a yellow oil
  5. distillationThe oil was distilled (bp1.2 mm 120° C.)
  6. customto give a cloudy yellow oil
  7. filtrationfiltered
  8. customthe solvent removed

Sources & evidence

ORD record
ord-202ff74c73484d83a6760d7d4ea508eb
Source dataset
uspto-grants-1982_10
Patent number
US04353908

Reaction notes

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