Sodium sulfate decahydrate → 9-Chloro-1-(2,4,6-trichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde

HRID 1399260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399260
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:30](OC)=[O:31])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=3[Cl:29])[CH2:18][CH2:19][CH2:20][N:13]21.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1.C(#N)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:30]=[O:31])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=3[Cl:29])[CH2:18][CH2:19][CH2:20][N:13]21

Komponenten

10

Edukt 4

HCID 62649Sodium sulfate decahydrateHCID 159087TriacetoxyperiodinaneHCID 21226445Aluminium lithium hydrideHCID 57786056HCID 57786056, Verbindung

Produkt 1

HCID 577858019-Chloro-1-(2,4,6-trichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a suspension of lithium aluminum hydride (53.7 mg, 1.42 mmol) in tetrahydrofuran (5 mL) was added a solution of methyl 9-chloro-1-(2,4,6-trichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (210 mg, 0.472 mmol) in tetrahydrofuran (5 mL) at 0° C., and the resultant mixture was stirred at 0° C. for 5 min. After sodium sulfate decahydrate (500 mg) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo to give a crude solid. To a solution of the crude solid in acetonitrile (5 mL) and dimethylsulfoxide (1 mL) was added Dess-Martin reagent (240 mg, 0.566 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 30 min, diluted with aqueous sodium bicarbonate and ethyl acetate, filtered and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (166 mg, 0.400 mmol, 85%).

Aufarbeitung

  1. filtrationthe resultant mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give a crude solid
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-15de23de4eb14f86b7273e289387331c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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