Cyanuric chloride → 6-cyclohexylamino-2,4-dichloro-1,3,5-triazine

HRID 413941Notes

Reaction equation

HRID 413941 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCOCC1.O>[CH:16]1([NH:22][C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 7965CyclohexylamineHCID 10340Sodium Carbonate

Product 1

HCID 5968536-cyclohexylamino-2,4-dichloro-1,3,5-triazineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
2.5 °C

Procedure

2,4,6-Trichloro-1,3,5-triazine (92.2 g) was dissolved in 300 mL of dioxane at room temperature. 53 g of Na2CO3 was dissolved in 300 mL of distilled water and was slowly added into the above solution. Cyclohexylamine (49.95 g) in a dropping funnel was slowly added into the above solution while stirring at 0-5° C. for 2 hr. The stirring was continued for another 3 hr at 0° C., 1 hr at room temperature, and the resultant white precipitate was then filtered and washed with water. The white precipitate was dissolved in methylenechloride (MC) and washed with water and MC was evaporated. Finally, 6-cyclohexylamino-2,4-dichloro-1,3,5-triazine having a substituted cyclohexyl was obtained after drying and solvent removal. The yield was more than 90%.

Workup

  1. additionwas slowly added into the above solution
  2. waitThe stirring was continued for another 3 hr at 0° C., 1 hr at room temperature
  3. filtrationthe resultant white precipitate was then filtered
  4. washwashed with water
  5. dissolutionThe white precipitate was dissolved in methylenechloride (MC)
  6. washwashed with water and MC
  7. customwas evaporated

Sources & evidence

ORD record
ord-f62161b6c2fd443692a97b8f78a736b7
Source dataset
uspto-grants-2003_05
Patent number
US06569916B2

Reaction notes

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