Cyanuric chloride → HCID 19869899, compound

HRID 1985995Notes

Reaction equation

HRID 1985995 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].[CH2:10]1[O:12][CH:11]1[CH2:13][OH:14].[OH-].[Na+]>ClCCl>[Cl:3][C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([O:14][CH2:13][CH:11]2[O:12][CH2:10]2)[N:1]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 11164GlycidolHCID 14798Sodium Hydroxide

Product 1

HCID 19869899HCID 19869899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 73.76 g (0.4 moles) cyanuric chloride in 360 ml of dichloromethane was chilled in an ice-water bath to about 0-5° C. and 31.85 g (0.43 moles) glycidol was added. A solution of 34.4 g 50% aqueous sodium hydroxide was added over about 30-45 minutes with stirring keeping the temperature between about 0° C. and about 10° C. Stirring was continued for an additional 3 hours after which time the layers were separated and the organic layer washed two times with water, and once with brine and the solution was dried over magnesium sulfate. Filtration and evaporation of the solution afforded a white solid, a sample of which was further purified by trituration with hexane-ethyl acetate. The proton and carbon nuclear magnetic resonance (NMR) spectra were consistent with the desired product, 2,4-dichloro-6-glycidoxy-1,3,5-triazine.

Workup

  1. customthe temperature between about 0° C. and about 10° C
  2. stirringStirring
  3. customafter which time the layers were separated
  4. washthe organic layer washed two times with water
  5. dry with materialonce with brine and the solution was dried over magnesium sulfate
  6. filtrationFiltration and evaporation of the solution
  7. customafforded a white solid
  8. customa sample of which was further purified by trituration with hexane-ethyl acetate

Sources & evidence

ORD record
ord-8a7569721b9c410aa8ee7e22c0060572
Source dataset
uspto-grants-2009_06
Patent number
US07547749B2

Reaction notes

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