2-Nitrobenzaldehyde → 2,6Dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5-phenylsulphonyl-1,4-dihydropyridine

HRID 328579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 328579
[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[C:5](\[NH2:7])/[CH3:6].[C:9]1([S:15]([CH2:18][C:19](=O)[CH3:20])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=O)([O-:24])=[O:23]>CN(C)P(=O)(N(C)C)N(C)C.C(OCC)(=O)C>[CH3:6][C:5]1[NH:7][C:19]([CH3:20])=[C:18]([S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH:27]([C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[N+:22]([O-:24])=[O:23])[C:4]=1[C:3]([O:2][CH3:1])=[O:8]

Komponenten

6

Edukt 3

HCID 111012-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 735827Phenylsulfonylacetone

Produkt 1

HCID 214428902,6Dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5-phenylsulphonyl-1,4-dihydropyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

6.9 g of 3-aminocrotonic acid methyl ester and 13.9 g of phenylsulphonylacetone are added to 9.1 g of o-nitrobenz- aldehyde dissolved in 50 ml of hexamethylphosphoric acid triamide. The mixture is then stirred for 10 hours under nitrogen at a bath temperature of 110° C. The mixture is cooled and dissolved in 400 ml of ethyl acetate and the solution is washed with a mixture of 400 ml of water, 60 ml of methanol and 60 ml of saturated sodium chloride solution. The aqueous phase is separated off and the organic phase is washed with 3 times 100 ml of water, with twice 100 ml of 1 N hydrochloric acid solution, with twice 60 ml of saturated sodium bicarbonate solution and once with 60 ml of 2 N sodium carbonate solution. The ethyl acetate phase is dried over sodium sulphate and evaporated. The residue is chromatographed on silica gel using a mixture of toluene and ethyl acetate (7:3) as the eluant. The eluate is evaporated and crystallised from methanol. In this way, 2,6dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5- phenylsulphonyl-1,4-dihydropyridine, of melting point 203° C, is obtained.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. washthe solution is washed with a mixture of 400 ml of water, 60 ml of methanol and 60 ml of saturated sodium chloride solution
  3. customThe aqueous phase is separated off
  4. washthe organic phase is washed with 3 times 100 ml of water, with twice 100 ml of 1 N hydrochloric acid solution, with twice 60 ml of saturated sodium bicarbonate solution and once with 60 ml of 2 N sodium carbonate solution
  5. dry with materialThe ethyl acetate phase is dried over sodium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel using
  8. additiona mixture of toluene and ethyl acetate (7:3) as the eluant
  9. customThe eluate is evaporated
  10. customcrystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-0c6c778086244c63bc4cd9a46c102e0a
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04017629

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