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

HRID 25050

Reaktionsgleichung

Reaktionsgleichung von HRID 25050
[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>[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 865860674-[[4-[(2,6-Dichlorophenyl)methyl]-6-(hydroxyamino)-1,3,5-triazin-2-yl]amino]benzonitrile monohydrochlorideAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fa5b6dad18684ef3900c0eadf2a4d808
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858609B2

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