Ammonia → 1,3,5-Triazine-2,4-diamine, 6-chloro-

HRID 365704Notes

Reaction equation

HRID 365704 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4]C=1Cl.[NH3:10].[C:11](#[N:13])C>>[NH2:10][C:5]1[N:4]=[C:11]([NH2:13])[N:1]=[C:8]([Cl:9])[N:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6342AcetonitrileHCID 7954Cyanuric chloride

Product 1

HCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-Yield 79%

Conditions

Temperature
0 °C

Procedure

To a solution obtained by dissolving 184.5 g (1.0 mol) of cyanuric chloride in 800 mL of acetonitrile at room temperature and cooling down to 0° C. was dropwise added over 2 hours 303.7 g (5.0 mol) of an aqueous 28% ammonia solution with vigorous stirring, by keeping the reaction temperature at 10° C. or lower. After completion of the dropwise addition, the cooling was discontinued and the mixture was stirred at room temperature for 1 hour, followed by gradually warming the mixture up to 45° C. and allowing the mixture to react for 4 hours. After cooling, the product was filtered and washed with a large amount of water. The filtrate was dried at 50° C. for 6 hours in vacuum to obtain 115 g (yield 79%) of the titled compound.

Workup

  1. customTo a solution obtained
  2. customat 10° C.
  3. additionAfter completion of the dropwise addition
  4. temperatureby gradually warming the mixture up to 45° C.
  5. customto react for 4 hours
  6. temperatureAfter cooling
  7. filtrationthe product was filtered
  8. washwashed with a large amount of water
  9. customThe filtrate was dried at 50° C. for 6 hours in vacuum

Sources & evidence

ORD record
ord-237ef95c48954736827beaebc4cc5d03
Source dataset
uspto-grants-2000_10
Patent number
US06127538

Reaction notes

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