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Sodium Methoxide → 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

HRID 35451
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 35451
[CH3:1][C:2]1([CH3:29])[C:13]2[C:5](=[CH:6][C:7]3[NH:8][C:9]([S:14][CH2:15][C:16]4[C:21]([CH3:22])=[C:20]([N+]([O-])=O)[CH:19]=[CH:18][N:17]=4)=[N:10][C:11]=3[CH:12]=2)[C:4]([CH3:27])([CH3:26])[C:3]1=[O:28].[CH3:30][O-:31].[Na+]>CO>[CH3:30][O:31][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:15][S:14][C:9]2[NH:8][C:7]3[CH:6]=[C:5]4[C:13](=[CH:12][C:11]=3[N:10]=2)[C:2]([CH3:29])([CH3:1])[C:3](=[O:28])[C:4]4([CH3:27])[CH3:26])[C:21]=1[CH3:22]
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Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 221514395,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

Produkt 1

HCID 98654732-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4.4 g (0.011 mol) of 5,7-dihydro-5,5,7,7-tetramethyl-2-[[(3-methyl -4-nitro-2-pyridyl)methyl)thio]indeno[5,6-d]imidazol-6(1H)-one in 100 ml of abs. methanol is treated with 3 g of sodium methylate, whereupon the mixture is boiled at reflux for 18 houre under argon. After concentrating the reaction mixture in vacuo the residue is treated with methylene chloride, whereupon the mixture is buffered by means of glacial acetic acid; the methylene chloride phase is extracted several times with a sodium bicarbonate solution, dried and evaporated. By recrystallisation from ethyl acetate there is obtained 5,7-dihydro-2-[[(4-methoxy-3 -methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one of melting point 222°-226°.

Aufarbeitung

  1. temperatureat reflux for 18 houre under argon
  2. concentrationAfter concentrating the reaction mixture in vacuo the residue
  3. additionis treated with methylene chloride, whereupon the mixture
  4. extractionthe methylene chloride phase is extracted several times with a sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customBy recrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3e5f115cd4dd48d3ae45ef8a0d1e2cb6
Quelldatensatz
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04766133

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