Sodium Carbonate → 4-Decanone

HRID 971754

Reaktionsgleichung

Reaktionsgleichung von HRID 971754
CS(O)(=O)=O.OCCCN1[C:14]2[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=2NC1=O.[C:21]1(N2C3(CCNCC3)C(=O)NC2)[CH:26]=CC=C[CH:22]=1.C(=O)([O-])[O-:39].[Na+].[Na+]>CN(C)C=O>[CH3:22][CH2:21][CH2:26][C:18](=[O:39])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:19]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 867353561,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one methanesulfonate

Produkt 1

HCID 122034-Decanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5.68 parts of 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one methanesulfonate, 4.62 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 3.7 parts of sodium carbonate and 45 parts of N,N-dimethylformamide is stirred for 1 hour at 60° C. The reaction mixture is cooled and poured onto water. The precipitated product is filtered off and purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of N,N-dimethylformamide and water, yielding 2 parts (24%) of 8-[3-(1,3-dihydro-5-methyl-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5[decan-4-one; mp. 255.5° C.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. filtrationThe precipitated product is filtered off
  4. custompurified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and 10% of methanol as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. customThe residue is crystallized from a mixture of N,N-dimethylformamide and water

Quellen und Nachweise

ORD-Eintrag
ord-847461700ade486b97da49aa5ea301e7
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04160836

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