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

HRID 2373991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2373991
[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-df6d5746ba8a40a39006c44210c73b1d
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07459562B2

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