Acetic Acid → 3-{5-[(3-Chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}pyridine

HRID 1668556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668556
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][NH:4][C:3]1=[S:13].Br[CH2:15][CH2:16][CH2:17][Cl:18].C(O)(=O)C>C(O)C>[Cl:18][CH2:17][CH2:16][CH2:15][S:13][C:3]1[N:2]([CH3:1])[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 80061-Bromo-3-chloropropaneHCID 7575824-methyl-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol

Produkt 1

HCID 534173103-{5-[(3-Chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 4-methyl-5-(3-pyridinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.4 g, preparation reported in WO 02/40471) in ethanol (6 ml) sodium ethanolate (0.85 ml) was carefully added with stirring followed by 1-bromo-3-chloropropane (0.31 ml). The mixture was heated at 90° C. for 1 h. Acetic acid was added at room temperature until pH=4. After elimination of the solvent under reduced pressure the residue was partitioned between aqueous NaHCO3 (saturated) and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated and submitted to column chromatography (EtOAc—acetone gradient) to provide the title compound as white solid (0.360 g).

Aufarbeitung

  1. customAfter elimination of the solvent under reduced pressure the residue was partitioned between aqueous NaHCO3 (saturated) and DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. concentrationThe combined DCM layers were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-29b55d647dbc4c9883f5c8428c22482e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989444B2

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