Sodium Thiosulfate → 9-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfonyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1399322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399322
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23]SCC)=[CH:4][CH:3]=1.Cl[C:28]1C=CC=C(C(OO)=O)[CH:29]=1.[S:38]([O-:42])([O-])(=[O:40])=S.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23][S:38]([CH2:28][CH3:29])(=[O:42])=[O:40])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 577863759-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfanyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

Produkt 1

HCID 577859309-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfonyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoleAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 9-Chloro-1-(2,4-dichlorophenyl)-6-[(ethylsulfanyl)methyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (216 mg, 0.506 mmol) in acetonitrile (10 mL) was added 3-chloroperbenzoic acid (70%, 0.274 g, 1.11 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hr. Aqueous sodium thiosulfate was added to the reaction mixture at 0° C. and the mixture was stirred at room temperature. The mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate and brine. The organic layer was concentrated in vacuo and the precipitated solid was collected by filtration. The solid was washed with water, 2-propanol and diisopropyl ether to give the title compound (190 mg, 0.414 mmol, 82%) as a colorless solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate and brine
  4. concentrationThe organic layer was concentrated in vacuo
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe solid was washed with water, 2-propanol and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-bc20534f2fc64070b461e5fd3cec3301
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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