Isoamyl Alcohol → HCID 19006814, compound

HRID 1742759Notes

Reaction equation

HRID 1742759 reaction equation
Cl[C:2]1[C:3](Cl)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH2:10]([OH:15])[CH2:11][CH:12]([CH3:14])[CH3:13]>>[CH3:13][CH:12]([CH3:14])[CH2:11][CH2:10][O:15][C:5]1[N:4]=[C:3]([O:15][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:2]=[C:7]([O:15][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[N:6]=1

Participants

3

Reactant 2

HCID 31260Isoamyl Alcohol2×HCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 19006814HCID 19006814, compoundYield 98.7%

Conditions

Temperature
50 °C

Procedure

49.5 g (0.45 mol) of sodium t-amylate are dissolved in 200 ml of isopentanol at 50° C., and 13 ml (0.11 mol) of trichloropyrimidine in 50 ml of isopentanol are added dropwise to this solution over the course of 30 minutes. After the mixture has been warmed at 50° C. for one hour, thin-layer chromatography shows that the mixture no longer contains any starting material. The solvent is removed on a rotary evaporator, and the residue is poured into 200 ml of water. The mixture is extracted three times with 150 ml of toluene in each case, and the organic phases are dried using MgSO4 and filtered. Removal of the solvent gives 37.5 g (98.7% of theory) of 2,4,6-tris(3-methylbut-1-oxy)pyrimidine.

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. additionthe residue is poured into 200 ml of water
  3. extractionThe mixture is extracted three times with 150 ml of toluene in each case
  4. customthe organic phases are dried
  5. filtrationfiltered
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-74acd09137134562b7c2295f4a6e0eec
Source dataset
uspto-grants-1994_08
Patent number
US05340701

Reaction notes

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