P-Phenylenediamine → N1-((2-(Pyridin-2-ylamino)thiazol-5-yl)methyl)benzene-1,4-diamine

HRID 2237213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2237213
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH:13]=O)=[CH:11][N:12]=1.[C:15]1([NH2:22])[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C([SiH](CC)CC)C>C(Cl)Cl.FC(C(O)=O)(F)F>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH2:13][NH:21][C:18]2[CH:19]=[CH:20][C:15]([NH2:22])=[CH:16][CH:17]=2)=[CH:11][N:12]=1

Komponenten

5

Edukt 3

HCID 7814P-PhenylenediamineHCID 12052TriethylsilaneHCID 220190582-(Pyridin-2-ylamino)thiazole-5-carbaldehyde

Produkt 1

HCID 59852979N1-((2-(Pyridin-2-ylamino)thiazol-5-yl)methyl)benzene-1,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of 2-(pyridine-2-ylamino)-thiazole-5-carbaldehyde (0.10 g, 0.49 mmol, WO2004/001059), benzene-1,4-diamine (0.105 g, 0.97 mmol) and triethylsilane (0.19 mL, 1.2 mmol) in CH2Cl2-TFA (3:1, 4 mL) was stirred at ambient temperature for 4 h. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution. The organic phase was washed with saturated aqueous NaHCO3 solution, brine, dried (MgSO4) and concentrated in vacuo. The crude product which contained the title compound along with the starting aldehyde and benzene-1,4-diamine was carried on directly into the next step.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution
  3. washThe organic phase was washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9fee4554637642e98fab57777a4c5ca1
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714138B2

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