Cyanuric chloride → 4-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 1062544Notes

Reaction equation

HRID 1062544 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].[Mg].Cl[C:13]1[N:18]=[C:17](Cl)[N:16]=[C:15]([Cl:20])[N:14]=1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>C(OCC)C.C1C=CC=CC=1.C(N(CC)C(C)C)(C)C.O1CCOCC1>[Cl:20][C:15]1[N:14]=[C:13]([CH2:2][C:3]2[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:10])[N:18]=[C:17]([NH:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[N:16]=1

Participants

9

Reactant 4

HCID 7954Cyanuric chlorideHCID 133964-AminobenzonitrileHCID 301591-Bromomethyl-2,6-dichlorobenzene2×HCID 5462224Magnesium

Product 1

HCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrileYield 104.2%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent3×HCID 312751,4-DioxaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 2-(bromomethyl)-1,3-dichlorobenzene (about 10% of 0.383 mol) in diethylether (240 ml) was added to magnesium (0.383 mol) in diethylether (240 ml) under argon. Once the reaction started, the remainder of 2-(bromomethyl)-1,3-dichlorobenzene in diethylether was added. The solution was stirred at RT for 2.5 hours and then added via canula to a solution of 2,4,6-trichloro-1,3,5-triazine (0.319 mol) in benzene (480 ml) while keeping the temperature below 15° C. The reaction mixture was stirred for one hour in an ice bath, then for 2 hours at RT. A solution of 4-amino-benzonitrile (0.351 mol) in N,N-diisopropylethylamine (61.0 ml) and 1,4-dioxane (500 ml) was added and the reaction mixture was stirred at RT for 40 hours. The solvent was evaporated. Water and ethylacetate were added. The solution was stirred, then the solid was filtered off, washed with ethylacetate and water, yielding 129.9 g of 4-[[4-chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile (intermediate 27; mp. 243-244° C.).

Workup

  1. customthe temperature below 15° C
  2. stirringThe reaction mixture was stirred for one hour in an ice bath
  3. waitfor 2 hours at RT
  4. stirringthe reaction mixture was stirred at RT for 40 hours
  5. customThe solvent was evaporated
  6. additionWater and ethylacetate were added
  7. stirringThe solution was stirred
  8. filtrationthe solid was filtered off
  9. washwashed with ethylacetate and water

Sources & evidence

ORD record
ord-621d5965a54e4e849771a2f0b0ec59b9
Source dataset
uspto-grants-2005_11
Patent number
US06962916B2

Reaction notes

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