Water → HCID 66554371, compound

HRID 512798Notes

Reaction equation

HRID 512798 reaction equation
[H-].[Na+].[CH3:3][C:4](=[CH2:8])[CH2:5][CH2:6][OH:7].Cl[C:10]1[N:15]=[C:14](Cl)[N:13]=[C:12](Cl)[N:11]=1.[OH2:18]>O1CCCC1>[CH3:8][C:4](=[CH2:3])[CH2:5][CH2:6][O:7][C:10]1[N:15]=[C:14]([O:18][CH2:6][CH2:5][C:4]([CH3:8])=[CH2:3])[N:13]=[C:12]([O:7][CH2:6][CH2:5][C:4]([CH3:3])=[CH2:8])[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 129883-Methyl-3-buten-1-olHCID 24758Sodium hydride

Product 1

HCID 66554371HCID 66554371, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 16.6 g of sodium hydride (purity: 60% or more), 600 mL of tetrahydrofuran was added and the resultant reaction mixture was cooled down to 0° C., followed by dropping 34.5 g of 3-methyl-3-buten-1-ol into the reaction mixture at 4° C. or less to be added. After the completion of the dropping, the resultant reaction mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was cooled down again to 0° C. and into the reaction mixture, 18.5 g of 2,4,6-trichloro-1,3,5-triazine dissolved in 110 mL of tetrahydrofuran was slowly dropped at 15° C. or less to be added. At room temperature, the reaction was effected over one night and to the reaction mixture, water was added, followed by extracting the resultant reaction mixture with ethyl acetate. The extract was washed with water and was dried over anhydrous sodium sulfate and from the extract, the solvent was distilled off to obtain 31.1 g of a crude product. The crude product was recrystallized (ethyl acetate:hexane=1:10) and the filtrate was purified with a column (ethyl acetate:hexane=1:4) to obtain 26.1 g of 2,4,6-tri(3-methyl-3-butene-1-oxy)-1,3,5-triazine which is the objective substance as a white solid. Yield: 76%, Purity: 97.0% (GC)

Workup

  1. customthe resultant reaction mixture
  2. customat 4° C. or less
  3. additionto be added
  4. customAfter the completion of the dropping, the resultant reaction mixture
  5. additionwas slowly dropped at 15° C. or less
  6. additionto be added
  7. additionwas added
  8. extractionby extracting the resultant
  9. customreaction mixture with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materialwas dried over anhydrous sodium sulfate and from the extract
  12. distillationthe solvent was distilled off
  13. customto obtain 31.1 g of a crude product
  14. customThe crude product was recrystallized (ethyl acetate:hexane=1:10)
  15. customthe filtrate was purified with a column (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-37246ce9d8ad4fa18d273410faf726ef
Source dataset
uspto-grants-2015_08
Patent number
US09102663B2

Reaction notes

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