N-(4-chlorophenyl)propanethioamide → [[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo4H-1,2,4-triazol-4-yl)phenyl]methyl]N-(4-chlorophenyl)propanimidothioate

HRID 1106694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1106694
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([O:14][CH3:15])=[N:12][N:11]([CH3:16])[C:10]1=[O:17].[Cl:18][C:19]1[CH:29]=[CH:28][C:22]([NH:23][C:24](=[S:27])[CH2:25][CH3:26])=[CH:21][CH:20]=1.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[CH3:15][O:14][C:13]1[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][S:27][C:24](=[N:23][C:22]2[CH:21]=[CH:20][C:19]([Cl:18])=[CH:29][CH:28]=2)[CH2:25][CH3:26])[C:10](=[O:17])[N:11]([CH3:16])[N:12]=1

Komponenten

6

Edukt 3

HCID 4154740N-(4-chlorophenyl)propanethioamideHCID 110338324-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 15457013[[2-(1,5-dihydro-3-methoxy-1-methyl-5-oxo4H-1,2,4-triazol-4-yl)phenyl]methyl]N-(4-chlorophenyl)propanimidothioateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.50 g of the title compound of Step D in 2 mL of THF was added 0.37 g of 4'-chlorothiopropionanilide and then 0.23 g of potassium tert-butoxide. (An exotherm occurred during this addition). The reaction was allowed to stir at room temperature overnight and then was heated briefly to reflux and allowed to cool. The reaction mixture was diluted with ethyl acetate and washed successively with water and then with saturated aqueous NaCl. The organic phase was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (50-60% ethyl acetate/hexanes) to afford 0.48 g of the title compound of Step E (about 95% pure), a compound of the invention. 1H NMR (CDCl3): δ 7.58 (m,1H), 7.37 (m,2H), 7.23 (m,3H), 6.60 (d,2H), 4.23 (s,2H), 3.86 (s,3H), 3.41 (s,3H).

Aufarbeitung

  1. addition(An exotherm occurred during this addition)
  2. temperaturewas heated briefly
  3. temperatureto reflux
  4. temperatureto cool
  5. washwashed successively with water
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (50-60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1dcc23cfbead4e749c25dc3754f588e5
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057352

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