Cyanuric chloride → HCID 23501186, compound

HRID 1294417Notes

Reaction equation

HRID 1294417 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.O1CCCC1.[NH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCOCC1>[Cl:9][C:4]1[N:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 133964-Aminobenzonitrile

Product 1

HCID 23501186HCID 23501186, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-75 °C

Procedure

2,4,6-trichloro-1,3,5-triazine (0.07440 mol) and tetrahydrofuran (100 ml) were combined and cooled to −75° C. under Ar atmosphere. 4-Aminobenzonitrile (0.07440 mol) was added and the solution was stirred for 4 hours at −75° C. Triethyl-amine (0.07440 mol) was added dropwise and the reaction mixture was allowed to warm up slowly to room temperature and stirred for 3 days. After adding 1,4-dioxane (100 ml), the resulting precipitate was collected by filtration, washed with tetrahydrofuran, and dried, yielding 12.74 g 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzonitrile (interm. 17). b) NaH (0.0113 mol), CH3CN (30 ml) and 2,6-dichlorophenol (0.0113 mol) were combined and stirred for 15 minutes under Ar atmosphere. Intermediate (17) (0.0113 mol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with ice water (30 ml) and filtered. A precipitate formed in the filtrate and was filtered off. The resulting solid was washed with H2O and CH3CN, then dried, yielding 0.62 g (14.0%) of 4-[[4-chloro-6-(2,6-dichloro-phenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile (interm. 18). c) N,N-Diisopropylethylamine (0.00714 mol) was added to a solution of 2-chloro-6-methylbenzenamine (0.00714 mol) in 1,4-dioxane (20 ml) under Ar flow. A solution of intermediate (17) (0.00714 mol) in 1,4-dioxane (5 ml) was added. The reaction mixture was stirred and refluxed for 24 hours. The solvent was evaporated and CH2Cl2 was added. The organic layer was washed with a saturated aqueous NaHCO3 solution, and the resulting precipitate was filtered, yielding 0.56 g (21.1%) of 4-[[4-chloro-6-[(2-chloro-6-methylphenyl)amino]-1,3,5-triazin-2-yl]amino]benzonitrile (interm. 19).

Workup

  1. temperatureto warm up slowly to room temperature
  2. stirringstirred for 3 days
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with tetrahydrofuran
  5. customdried

Sources & evidence

ORD record
ord-7c6d08eb0cf24bc5b9f195c2a2904502
Source dataset
uspto-grants-2007_07
Patent number
US07241458B1

Reaction notes

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