Sodium Chloride → 4,6-Dichloro-N,N-diethyl-1,3,5-triazin-2-aminato

HRID 1590955Notes

Reaction equation

HRID 1590955 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[OH-].[Na+].[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].[Cl-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:14]([CH2:15][CH3:16])[CH2:12][CH3:13])[N:7]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7954Cyanuric chlorideHCID 8021DiethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 744054,6-Dichloro-N,N-diethyl-1,3,5-triazin-2-aminatoYield 70.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 50.0 g (271 mmol) of cyanuric chloride, 22.0 g of 50% aqueous sodium hydroxide, 22 ml of water, and 150 ml of toluene, cooled to 0° C., is admixed with a solution of 19.8 g (271 mmol) of diethylamine in 25 ml of toluene over a 45 minute interval. The reaction temperature is maintained at 0°-5° C. throughout the addition. After the addition is complete, the reaction mixture is stirred for two hours at ambient temperature. Water is added to the mixture to dissolve the sodium chloride, and the phases are separated. The organic phase is dried over magnesium sulfate and concentrated to give an oil which is crystallized from heptane to give 42.0 g (70% yield) of 2,4-dichloro-6-diethylamino-1,3,5-triazine, a white crystalline material, m.p. 77°-9° C.

Workup

  1. temperatureThe reaction temperature is maintained at 0°-5° C. throughout the addition
  2. additionAfter the addition
  3. customthe phases are separated
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oil which
  7. customis crystallized from heptane

Sources & evidence

ORD record
ord-e1b5e6a41016429781451dd3f80a6300
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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