4-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile → 4-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile monohydrochloride monohydrate

HRID 270630Notes

Reaction equation

HRID 270630 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:3]=1.C[Si](C)(C)[O:28][NH2:29]>O1CCOCC1>[OH2:28].[ClH:1].[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[CH2:8][C:6]1[N:7]=[C:2]([NH:29][OH:28])[N:3]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:5]=1

Participants

4

Reactant 2

HCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrileHCID 2734666O-(Trimethylsilyl)hydroxylamine

Product 1

HCID 222816854-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile monohydrochloride monohydrateYield 59.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Intermediate (27) (0.0128 mol), 1,4-dioxane (50 ml), and O-(trimethylsilyl)hydroxyl-amine, (0.134 mol) were combined under argon. The reaction mixture was stirred at RT for 20 hours. The reaction mixture was concentrated and DCM (50 ml), NaOH (1 N; 50 ml), and HCl (1N; 100 ml) were added. The solution was stirred for one hour. The precipitate was filtered off and recrystallized from methanol. The precipitate was filtered off and dried, yielding 2.96 g (59.8%) of 4-[[4-[(2,6-dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile monohydrochloride monohydrate (compound 21).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionDCM (50 ml), NaOH (1 N; 50 ml), and HCl (1N; 100 ml) were added
  3. stirringThe solution was stirred for one hour
  4. filtrationThe precipitate was filtered off
  5. customrecrystallized from methanol
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-b22032755bc345b19d2f93b4b5e41810
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Reaction notes

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