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

HRID 1955168Notes

Reaction equation

HRID 1955168 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].C(=O)([O-])O.[K+].[NH3:20]>O.C(#N)C>[NH2:20][C:8]1[N:1]=[C:2]([NH:14][CH2:10][CH2:11][CH2:12][CH3:13])[N:4]=[C:5]([Cl:6])[N:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7954Cyanuric chlorideHCID 8007ButylamineHCID 516893Potassium Bicarbonate

Product 1

HCID 119704791,3,5-Triazine-2,4-diamine, N-butyl-6-chloro-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Into a four-necked flask equipped with a stirrer, a thermometer and a condenser, 18.5 g (0.1 mol) of cyanuric chloride and 150 ml of acetonitrile were dissolved at room temperatures, followed by adding dropwise a mixed solution containing of 7.3 g (0.1 mol) of n-butyl amine and 20 g of an ion-exchanged water over 2 hours while maintaining at a reaction temperature of not more than 5° C. After that, a solution containing of 10 g (0.1 mol) of potassium hydrogen carbonate and 40 g of an ion-exchanged water was added dropwise over 1 hour while maintaining the temperature at not more than 5° C., followed by adding dropwise 15.2 g (0.25 mol) of 28% aqueous ammonia at the same temperature and stirring at 50° C. for 4 hours after gradually heating. After that, a product was filtered and washed with a large quantity of an ion-exchanged water, followed by drying in vacuo to obtain 2-amino-4-butylamino-6-chloro-1,3,5-triazine which is an intermediate raw material. Total quantity of the raw material was dispersed into 100 g of an ion-exchanged water, followed by adding 8.1 g (0.11 mol) of n-butyl amine and raising the temperature to a reflux temperature while stirring and reacting for 2 hours. Further, a solution containing 4.0 g (0.1 mol) by weight of sodium hydroxide and 20 g of an ion-exchanged water was dropwise added over 1 hour, followed by allowing to react at the reflux temperature for 2 hours. After cooling to room temperatures, a product was extracted with 100 ml of toluene, and an organic layer was washed five times with 80 ml of an ion-exchanged water, followed by distilling off solvents at reduced pressure to obtain 27 g of 2-amino-4,6-bis(monobutylamino)-1,3,5-triazine.

Workup

  1. customInto a four-necked flask equipped with a stirrer
  2. additionby adding dropwise a mixed solution
  3. temperaturewhile maintaining at a reaction temperature of not more than 5° C
  4. additionwas added dropwise over 1 hour
  5. temperaturewhile maintaining the temperature at not more than 5° C.
  6. temperatureafter gradually heating
  7. filtrationAfter that, a product was filtered
  8. washwashed with a large quantity of an ion-exchanged water
  9. customby drying in vacuo

Sources & evidence

ORD record
ord-0cd519407a904c38993c5086834b1711
Source dataset
uspto-grants-2000_09
Patent number
US06124381

Reaction notes

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