2-(Chloromethyl)-3-methylpyridine → 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

HRID 35453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35453
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]3[C:12](=[CH:13][C:4]=2[N:3]=1)[C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[C:9]3([CH3:18])[CH3:17].C([O-])(C)(C)C.[K+].Cl[CH2:26][C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=1.C(OCC)(=O)C.CCCCCC>C(O)(C)(C)C>[CH3:15][C:11]1([CH3:14])[C:12]2[C:8](=[CH:7][C:5]3[NH:6][C:2]([S:1][CH2:26][C:27]4[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=4)=[N:3][C:4]=3[CH:13]=2)[C:9]([CH3:18])([CH3:17])[C:10]1=[O:16]

Komponenten

6

Edukt 4

HCID 130586822-(Chloromethyl)-3-methylpyridineHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxideHCID 178429018HCID 178429018, Verbindung

Produkt 1

HCID 704258435,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A suspension of 5.2 g of 5.7-dihydro-2-mercapto-5,5,7,7 -tetramethylindeno[5,6-d]imidazol-6(1H )-one and 2.6 g of potassium t-butanolate is treated under argon with a solution of 3 g of 2-chloromethyl-3-methylpyridine in 30 ml of t-butanol and the mixture is stirred for 18 hours. After concentrating the mixture the residue is acidified with glacial acetic acid and dissolved in methylene chloride, whereupon 10% sodium bicarbonate solution is added thereto. the mixture is extracted and the methylene chloride solutlon is dried and concentrated. The thus-obtained crude product is chromatographed on silica gel and purified with methylene chloride/ethyl acetate (1:1), the medium pressure flash chromatography method being used and the pressure being produced with nitroqen gas. The 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-2 -pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H )-one which is obtained from ethyl acetate-n-hexane melts at 161°-164°.

Aufarbeitung

  1. concentrationAfter concentrating the mixture the residue
  2. dissolutiondissolved in methylene chloride, whereupon 10% sodium bicarbonate solution
  3. additionis added
  4. extractionthe mixture is extracted
  5. dry with materialthe methylene chloride solutlon is dried
  6. concentrationconcentrated
  7. customThe thus-obtained crude product
  8. customis chromatographed on silica gel
  9. custompurified with methylene chloride/ethyl acetate (1:1)
  10. customthe pressure being produced with nitroqen gas

Quellen und Nachweise

ORD-Eintrag
ord-d7bdef4d67254c71b6bd0a37201da9a6
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766133

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