Cyanuric chloride → HCID 23501189, compound

HRID 1294418Notes

Reaction equation

HRID 1294418 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[NH2:18].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[NH:18][C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 118462,6-Dichloroaniline

Product 1

HCID 23501189HCID 23501189, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,4,6-Trichloro-1,3,5-triazine (0.0266 mol) was added to 1,4-dioxane (50 ml) under Ar atmosphere. The solution was stirred until it became homogeneous, then 2,6-dichlorobenzenamine (0.0266 mol) and K2CO3 (0.0362 mol) were added. The reaction mixture was stirred at room temperature for 3 days. The solvent was evaporated. Water was added to the residue and the aqueous phase was extracted with CH2Cl2. The separated organic layer was washed with brine, dried with potassium carbonate, filtered and the filtrate was evaporated, yielding 7.52 g (91.2%) of N-(2,6-dichlorophenyl)-4,6-dichloro-1,3,5-triazin-2-amine (interm. 20). b) 1,4-Dioxane (50 ml), 4-cyanoaniline (0.0243 mol), and N,N-diisopropylethylamine (0.0243 mol) were added to intermediate (20) (0.0243 mol) under Ar atmosphere. The reaction mixture was stirred and refluxed for 1 week. The reaction was cooled, the solvent was evaporated and the residue was dissolved in ethyl acetate. The organic phase was washed with a saturated NaHCO3 solution and with brine, dried with potassium carbonate, filtered, and the solvent was evaporated. The residue was stirred in a mixture of CH2Cl2 and saturated NaHCO3, and the precipitate filtered, yielding 2.26 g (23.8%) of 4-[[4-chloro-6-[(2,6-dichlorophenyl)amino]-1,3,5-triazin-2-yl]amino]benzonitrile (interm. 21).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 days
  2. customThe solvent was evaporated
  3. additionWater was added to the residue
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried with potassium carbonate
  7. filtrationfiltered
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fd70b321b18e41d7ac46e425c50a4f1f
Source dataset
uspto-grants-2007_07
Patent number
US07241458B1

Reaction notes

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