Cyanuric chloride → 6-Chloro-N~2~,N~4~-dioctyl-1,3,5-triazine-2,4-diamine

HRID 1583921Notes

Reaction equation

HRID 1583921 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[CH2:10]([NH2:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[K+]>CC(C)=O>[CH2:10]([NH:18][C:2]1[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([NH:18][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[N:4]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 8143OctylamineHCID 14797Potassium Hydroxide

Product 1

HCID 183563846-Chloro-N~2~,N~4~-dioctyl-1,3,5-triazine-2,4-diamineYield 64.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

37 g (0.2 mol) of cyanuric chloride was dissolved in 80 ml of hot acetone and the solution was rapidly added to 120 ml of ice water (crushed ice:water=1:1) with vigorous stirring. The temperature reached 0° to 5° C. 56.8 g (0.44 mol) of n-octylamine was gradually added dropwise while maintaining the temperature at 10° C. or below. Then, the temperature was raised to 40° C. by heating and the mixture was heated on a water bath for 1 hour. Since the pH of the reaction solution turned into the acid region (pH<2), granules of potassium hydroxide was gradually added to maintain the pH around neutral (the time required was 1 hour). The product deposited in the reaction solution was cooled and separated by filtration. The crystals were thoroughly washed with water and dried. The crude crystals were recrystallized from ethanol to obtain 48 g of Intermediate A having a melting point of 171°-172° C.

Workup

  1. customreached 0° to 5° C
  2. temperaturewhile maintaining the temperature at 10° C. or below
  3. temperatureby heating
  4. temperaturethe mixture was heated on a water bath for 1 hour
  5. additionwas gradually added
  6. temperatureto maintain the pH around neutral (the time
  7. temperaturewas cooled
  8. customseparated by filtration
  9. washThe crystals were thoroughly washed with water
  10. customdried
  11. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-342977f1428543b290e0bc67d2afc5da
Source dataset
uspto-grants-1985_11
Patent number
US04555479

Reaction notes

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