m-Chloroperbenzoic acid → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfinyl)methyl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717359
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=3)[C:11]=2[CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:6])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:39])C=1>C1COCC1.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([NH:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:25]=3)[C:11]=2[CH2:12][S:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:39])=[O:6])[CH2:2][CH2:3]1

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 57664805N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylthio)methyl]-1H-1,2,3-triazole-4-carboxamide

Produkt 1

HCID 57665018N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfinyl)methyl]-1H-1,2,3-triazole-4-carboxamideAusbeute 25,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylthio)methyl]-1H-1,2,3-triazole-4-carboxamide (145 mg, 0.344 mmol) obtained in Example 130 was dissolved in THF (3.0 ml), m-chloroperbenzoic acid (purity 65%, 110 mg, 0.412 mmol, 1.2 eq.) was added with stirring at 0° C., and the mixture was stirred for additional 1.5 hr. The reaction mixture was diluted with ethyl acetate (20 ml), washed with 5% aqueous sodium sulfite solution, 2% aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:1-5:1) on silica gel (manufactured by E. Merck, Art.7734, 10 g). The fraction obtained by elution with ethyl acetate-hexane (5:1) was concentrated, and diethyl ether was added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (38 mg, 0.087 mmol, 25.3%).

Aufarbeitung

  1. stirringthe mixture was stirred for additional 1.5 hr
  2. washwashed with 5% aqueous sodium sulfite solution, 2% aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washThe residue was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:1-5:1) on silica gel (manufactured by E. Merck, Art.7734, 10 g)
  6. customThe fraction obtained by elution with ethyl acetate-hexane (5:1)
  7. concentrationwas concentrated
  8. additiondiethyl ether was added
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with diethyl ether
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6245007954874ac6a1bf833c627ca201
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803822B2

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