Cyanuric chloride → 4,6-Dichloro-N-cyclopropyl-1,3,5-triazin-2-amine

HRID 28109Notes

Reaction equation

HRID 28109 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.[OH-].[Na+]>ClC1C=CC=CC=1>[CH:10]1([NH:13][C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 69828Cyclopropylamine

Product 1

HCID 222540664,6-Dichloro-N-cyclopropyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
-10 °C

Procedure

133 g of cyanuric chloride are suspended in 720 ml of chlorobenzene and cooled to -10° C. To this suspension are added with stirring 50 ml of cyclopropylamine dropwise over a period of 25 minutes. Keeping the temperature at -10° C., 96 ml of aqueous sodium hydroxide (30% NaOH) are added dropwise. The reaction mixture is then stirred at -10° C. for 11/2 hours and allowed to stand for a further 16 hours at room temperature, after which it is washed with water (2×400 ml), dried over anhydrous sodium sulphate and filtered. The excess chlorobenzene is then removed by water jet vacuum distillation. 138 g of 2-cyclopropylamino-4,6-dichloro-s-triazine in the form of white crystals are obtained.

Workup

  1. additionTo this suspension are added
  2. customat -10° C.
  3. waitto stand for a further 16 hours at room temperature
  4. washafter which it is washed with water (2×400 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customThe excess chlorobenzene is then removed by water jet vacuum distillation

Sources & evidence

ORD record
ord-8cad7758f10c4a5abd3dddc305038682
Source dataset
uspto-grants-1980_09
Patent number
US04225598

Reaction notes

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