Guanidine → HCID 178510034, compound

HRID 1062554Notes

Reaction equation

HRID 1062554 reaction equation
[OH-].[Na+].[NH2:3][C:4]([NH2:6])=[NH:5].Cl[C:8]1[N:13]=[C:12]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[N:11]=[C:10]([NH:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[N:9]=1>O1CCOCC1>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([NH:23][C:10]2[N:11]=[C:12]([CH2:14][C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[N:13]=[C:8]([NH:5][C:4]([NH2:6])=[NH:3])[N:9]=2)=[CH:25][CH:26]=1)#[N:29]

Participants

5

Reactant 3

HCID 3520GuanidineHCID 14798Sodium HydroxideHCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Product 1

HCID 178510034HCID 178510034, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

NaOH (0.0128 mol), 1,4-dioxane (5 ml), and guanidine (0.0128 mol) were combined and stirred at RT for 5 minutes under argon. Then, intermediate (27) (0.00128 mol) was added and the reaction mixture was stirred at RT for 16 hours. The reaction mixture was quenched with H2O, and stirred. The resulting precipitate was filtered off and the residue was stirred in refluxing methanol, cooled, and filtered, yielding 0.34 g (64.3%) of N-[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]guanidine (compound 20).

Workup

  1. stirringthe reaction mixture was stirred at RT for 16 hours
  2. customThe reaction mixture was quenched with H2O
  3. stirringstirred
  4. filtrationThe resulting precipitate was filtered off
  5. stirringthe residue was stirred
  6. temperaturein refluxing methanol
  7. temperaturecooled
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ec57c0cc20634eb88cd9b2a43a7c1abd
Source dataset
uspto-grants-2005_11
Patent number
US06962916B2

Reaction notes

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