Hydrochloric Acid → 3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

HRID 2196604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196604
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[SH:7].CC(C)([O-])C.[K+].Cl[C:15]1[N:20]=[C:19]([C:21]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[N:25]=2)=[O:22])[C:18]([S:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[CH:17][CH:16]=1.Cl>O.C(Cl)(Cl)Cl.CC(N(C)C)=O>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([S:30][C:18]2[C:19]([C:21]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH3:29])[N:25]=3)=[O:22])=[N:20][C:15]([S:7][C:3]3[N:2]([CH3:1])[CH:6]=[N:5][N:4]=3)=[CH:16][CH:17]=2)=[CH:32][CH:33]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 866196096-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamideHCID 178481306HCID 178481306, Verbindung

Produkt 1

HCID 597062523-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamideAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

20 g of 4-methyl-4H-1,2,4-triazole-3-thiol and 19 g of potassium t-butoxide were added to a dimethylacetamide (130 ml) solution of 13 g of 6-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide, and stirred under heat at 160° C. for 8 hours. At room temperature, chloroform and water were added to it, and its pH was controlled to 3 with aqueous 1 N hydrochloric acid solution added thereto. This was extracted with chloroform, and the organic layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol) to obtain 10.0 g of the entitled compound as a yellow solid.

Aufarbeitung

  1. additionadded
  2. extractionThis was extracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-3b4e3bc0593b4f3c889d066f101fb31e
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338460B2

Notizen zur Reaktion

Wird geladen…