Cyanuric chloride → 2-Chloro-4,6-bis[(oxiran-2-yl)methoxy]-1,3,5-triazine

HRID 330348Notes

Reaction equation

HRID 330348 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[O:10]1[CH2:14][CH:11]1[CH2:12][OH:13].[OH-:15].[Na+]>C(Cl)(Cl)Cl>[Cl:3][C:2]1[N:4]=[C:5]([O:13][CH2:12][CH:11]2[O:10][CH2:14]2)[N:7]=[C:8]([O:15][CH2:12][CH:11]2[O:10][CH2:14]2)[N:1]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 11164GlycidolHCID 14798Sodium Hydroxide

Product 1

HCID 187799312-Chloro-4,6-bis[(oxiran-2-yl)methoxy]-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mechanically stirred solution of 220.8 g (1.2 mol) cyanuric chloride in 1500 ml chloroform, cooled to 0°-10° C., was added 266.4 g (3.6 mol) 2,3-epoxy-1-propanol in one portion. Aqueous sodium hydroxide (50% solution; 192 g) was added to the mixture dropwise with stirring over about 3 hr maintaining the reaction temperature below 10° C. and preferably around 0°-5° C. The reaction mixture was allowed to warm slowly to room temperature. The chloroform layer was washed with distilled water until neutral and dried over magnesium sulfate. The reaction product was found by nuclear magnetic resonance to be 2-chloro-4,6-diglycidoxy-1,3,5-triazine. Analysis showed about 95% (by weight) chlorodiglycidoxytriazine. The reaction mixture also was found to contain small amounts of triglycidoxytriazine and dichloro monoglycidoxytriazine.

Workup

  1. temperaturemaintaining the reaction temperature below 10° C. and preferably around 0°-5° C
  2. washThe chloroform layer was washed with distilled water until neutral and
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-082ba3701cbf478cab5efa205c7b6b08
Source dataset
uspto-grants-1990_01
Patent number
US04895945

Reaction notes

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