Disilathiane, 1,1,1,3,3,3-hexamethyl- → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbothioamide

HRID 420896

Reaktionsgleichung

Reaktionsgleichung von HRID 420896
C[Si](C)(C)[S:3][Si](C)(C)C.C[O-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([Cl:24])[C:15]=1[N:25]1[C:29]([NH:30][CH3:31])=[C:28]([CH:32]2[S:36][CH2:35][CH2:34][S:33]2)[C:27]([C:37]#[N:38])=[N:26]1>CN(C)C=O.CCOCC.O>[Cl:24][C:16]1[CH:17]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:19]=[C:14]([Cl:13])[C:15]=1[N:25]1[C:29]([NH:30][CH3:31])=[C:28]([CH:32]2[S:33][CH2:34][CH2:35][S:36]2)[C:27]([C:37](=[S:3])[NH2:38])=[N:26]1

Komponenten

7

Edukt 3

HCID 76920Disilathiane, 1,1,1,3,3,3-hexamethyl-HCID 10942334Sodium MethoxideHCID 231319151-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 231319131-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbothioamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To 1,1,1,3,3,3-hexamethyldisilathiane (0.157 g, 0.9 mmol) in dimethylformamide (4 mL) was added sodium methoxide (0.049 g, 0.9 mmol) and the resulting mixture was sonicated to provide a homogeneous blue colored solution. This resulting solution was added to the solution of 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbonitrile (0.08 g, 0.2 mmol) in dimethylformamide (5 mL) at room temperature under nitrogen. This mixture was stirred at room temperature for one and half hour. It was then diluted with ether (30 mL) and water (30 mL). The layers were separated and the aqueous layer was extracted with ether. The ethereal layers were combined and washed twice with water (2×20 mL), dried (Na2SO4), and concentrated to provide a yellow solid. Upon chromatographic purification via silica gel eluting with heptane:ethyl acetate (4:1 to 2:1), a yellow solid (0.048 g, 55%) was obtained. 19F-NMR: −63.634.

Aufarbeitung

  1. customthe resulting mixture was sonicated
  2. customto provide a homogeneous blue colored solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether
  5. washwashed twice with water (2×20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto provide a yellow solid
  9. customUpon chromatographic purification via silica gel eluting with heptane:ethyl acetate (4:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f8f2fcccba364f3b87683540c273c7ca
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097732B2

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